Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 113118-81-3, 5-Bromonicotinaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 113118-81-3, blongs to pyridine-derivatives compound. Recommanded Product: 113118-81-3

To a solution of 5-bromonicotinaldehyde (XXV) (5.0 g, 26.9 mmol) in DCE (108 mL) was added dimethylamine-HCl (4.39 g, 53.8 mmol) and TEA (7.5 g, 53.8 mmol). The reaction was stirred at room temperature for 1 h. NaBH(OAc)3 was added and the reaction was stirred overnight at room temperature. The reaction was diluted with DCM and sat. aq. NaHCC . The organic layer was separated, washed with water, brine, dried and concentrated under vacuum to produce l-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine (XXVI) as a brown liquid (92.6% yield). NMR (CDCI3) delta ppm 2.15 (s, 6H), 3.43 (s, 2H), 7.94 (s, 1H), 8.47 (d, J=2Hz, 1H), 8.59 (d, J=3Hz, 1H); ESIMS found for C8HnBrN2 mlz 215 (MBr79+H) and 217 (MBl81+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-81-3, its application will become more common.

Reference:
Patent; SAMUMED, LLC; DESHMUKH, Vishal; MURPHY, Eric Anthony; HOOD, John; (232 pag.)WO2018/75858; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7598-35-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7598-35-8, name is 2-Bromopyridin-4-amine. A new synthetic method of this compound is introduced below.

To a solution of 2-bromopyridin-4-amine (75 g, 433 mmol) in pyridine (750 mL) stirred under nitrogenat 0C was added 2,5-dichloropyridine-3-sulfonyl chloride (128 g, 520 mmol) portionwise. The reactionmixture was stirred at room temperature for 16 h. After this time, pyridine was evaporated under reduced pressure to obtain a crude residue which was poured into ice water. The resulting solid was collected by filtration and dried. The solid was dissolved in EtOAc (2 L) and the organic layer was washed with 10% EDTA solution (2 L). The organic phase was dried over Na2SO4, filtered andconcentrated under reduced pressure to afford the title compound (120 g) as a brown solid. LCMS (Method G) Rt = 2.16 mi [M+H] = 381.9/383.9/385.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7598-35-8, 2-Bromopyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (157 pag.)WO2017/137535; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 126053-15-4, Adding some certain compound to certain chemical reactions, such as: 126053-15-4, name is 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol,molecular formula is C8H8ClNO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 126053-15-4.

A solution of intermediate 38 (0.92 mmol), 4-chloro-6,7-dihydro- 5/-/-cyclopenta[b]pyridin- 7-ol (1 mmol), hydrogen chloride in dioxane 4M (46mul) in CH3CN (10ml) was heated at 65C for 5 hours. K2CO3 10% aqueous solution and EtOAc were added. The reaction mixture was extracted, the organic layer was separated, dried over MgSO4, filtered and evaporated. The residue (0.4g) was purified by high-performance liquid chromatography (Stability Silica 5mum 150×30. Omm). Mobile phase (NH4OH 0.2%; gradient CH2CI2/CH3OH from 98/2 to 88/12), yielding 49mg compound 63 and 114mg of compound 64.

According to the analysis of related databases, 126053-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37308; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1121-76-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1121-76-2, name is 4-Chloropyridine 1-oxide, molecular formula is C5H4ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-Chloropyridine-N-oxide (3.0 g, 23 mmol), 4-trifluoromethylphenylboronic acid (6.57 g, 34.6 mmol), K2CO3 (4.8 g, 35 mmol) and PdCl2(dppf) (470 mg, 0.57 mmol) were stirred in DMSO (40 mL) under vacuum for 30 min. The flask was flushed with nitrogen, and the mixture was heated to 80 C. for 10 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (1.90 g, 34%) as a tan solid: ESI MS m/z 240 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 101083-92-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 101083-92-5, name is 5-Nitro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

2.675 g 5-Nitro-lH-pyrrolo[2,3-b]pyridine in 200 ml THF were hydrogenated over 1.0 g Platinum on carbon at atmospheric pressure for 3 hrs at RT (with thin layer chromatography (TLC) control). The catalyst was removed by filtration, the filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetate /heptane mixtures. Yield 1.84 g

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101083-92-5, 5-Nitro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/28617; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13362-26-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13362-26-0, name is Ethyl 2-aminonicotinate, molecular formula is C8H10N2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of ethyl 2-aminopyridine-3-carboxylate (1) (4.28 g, 25.8 mmol, Zhou, Z. L and al. Bioorg. Med. Chem. 2001, 9, 2061-2071) in 1,2-dimethoxyethane (DME) (100 mL) was added dropwise a solution of 1,1,3-trichloracetone (8.32 g, 51.5 mmol) in DME (15 mL). The mixture was stirred at room temperature for 76 h. The resulting precipitate was collected by filtration and washed with DME (2×15 mL). The solid was poured into dry ethanol (100 mL) and heated under reflux for 18 h. The cooled solution was evaporated and an aqueous saturated NaHCO3 solution (40 mL) was added. The mixture was extracted with CH2Cl2 and the organic layers were dried (MgSO4), filtered and evaporated to dryness. The residue was purified by chromatography using CH2Cl2 as eluent to give in order of elution: dichloro compound 2h (4.95 g, 70%); mp 108-110 C.; IR (KBr) 1719, 1279 cm-1; 1H NMR (200 MHz, CDCl3) delta 1.44 (t, 3H, J=7 Hz), 4.51 (q, 2H, J=7 Hz), 6.99 (t, 1H, J=7 Hz), 7.12 (s, 1H), 8.03 (m, 2H), 8.39 (d, 1H, J=7 Hz); 13C NMR (100 MHz, CDCl3) delta 14.3, 62.0, 65.3, 112.0, 112.7, 120.3, 130.3, 130.7, 141.6, 146.3, 163.5. MS m/z 276 (M++4, 2), 274 (M++2, 13), 272 (M+, 17), 237 (29), 202 (63), 200 (100), 166 (27), 129 (47).

According to the analysis of related databases, 13362-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universite D’Auvergne Clermont 1; Universite Francois Rabelais Tours; Katholieke Universiteit Leuven; US2010/93781; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, name: 2-Amino-5-bromonicotinic acid, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinic acid

Step 2: 5-Bromo-3-(3-(2,2,2-trifluoroethyl)-1 ,2,4-oxadiazol-5-vl)pyridin-2-amine To a stirring suspension of 2-amino-5-bromonicotinic acid (2.3 g, 10.60 mmol) in DCM (53.0 ml), 1-chloro-N,N,2-trimethyl-1-propenylamine (Ghosez’s reagent) (1.683 ml, 12.72 mmol) was added. The reaction mixture was left stirring for 1.5 hours. 3,3,3-trifluoro-N’- hydroxypropanimidamide (step 1) (1.656 g, 11.66 mmol) was then added followed by DIPEA (3.70 ml, 21.20 mmol). The reaction mixture was stirred overnight. T3P (18.56 ml, 31.8 mmol) was added to the mixture and this was microwaved for 3 hours at 100C. The mixture was added to water (100ml) and product extracted into EtOAc (2 x 90ml). The organic extracts were washed with brine, dried over MgS04 and the filtrate was concentrated under reduced pressure. The crude product was purified by adding MeOH (~10ml). The mixture was sonicated and the resulting solid collected by filtration, washed with MeOH and dried to afford the title compound; LCMS: Rt = 1.17 mins; MS m/z 325.0 [M+H]+; Method 2minLowpHv01 1H NMR (400 MHz, DMSO-d6) delta 8.40 (1 H, d), 8.35 (1 H, d), 7.59 (2H, br s), 4.21 (2H, q).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52833-94-0, 2-Amino-5-bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; WO2015/162456; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52334-90-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.52334-90-4, name is 3-Methoxypyridin-4-amine, molecular formula is C6H8N2O, molecular weight is 124.1405, as common compound, the synthetic route is as follows.

Under an atmosphere of argon, 60.0 mg (0.16 mmol) of 5-{[6-(2-fluorophenyl)pyridin-3- yl]carbamoyl}-2-methoxybenzoic acid (intermediate 23) and 24.4 mg (0.20 mmol) of 3-methoxypyridin-4-amine were dissolved in 3.94 mL of anh DMF. 86 ilL (0.49 mmol) of N-ethyl-Nisopropylpropan-2-amine and 102.3 mg (0.20 mmol) of PYBOP were added and it was stirred at rt over night. The reaction mixture was concentrated on a rotavap and the residue was purified py HPLC (Waters XBrigde C18 5j1 lOOx3Omm; water + 0.2% vol. ammonia (32%) / acetonitril gradient; temperature: room temperature; injection: 250 ilL; DAD scan: 210-400 nm) affording 24.2 mgmaterial which was impure and was purified further by HPLC (method 5) giving 2 mg (2% of theory) of the title compound.?H-NMR (300 MHz, DMSO-d6) 6 [ppm]: 2.270 (2.86), 2.725 (2.86), 3.884 (1.56), 4.085 (16.00), 4.196 (15.35), 7.297 (1.82), 7.336 (5.07), 7.365 (4.03), 7.437 (1.69), 7.460 (2.86), 7.488 (4.68), 7.518 (3.90),7.820 (2.73), 7.848 (2.86), 7.943 (1.69), 7.970 (2.73), 7.996 (1.56), 8.216 (2.60), 8.236 (3.12), 8.273 (2.60), 8.310 (3.77), 8.346 (2.60), 8.392 (4.68), 8.407 (7.15), 8.783 (4.42), 9.093 (4.29), 10.709 (4.29), 10.758 (4.68).LC-MS (Method 3): R = 1.19 mm; MS (ESIpos): m/z = 473 [M+H].

Statistics shows that 52334-90-4 is playing an increasingly important role. we look forward to future research findings about 3-Methoxypyridin-4-amine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; (130 pag.)WO2016/131794; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17368-12-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17368-12-6 as follows.

A solution of 2-chioropyridin-4-ol (1.0 g, 7.72 mmoi) in DMF (20 rnL) was treated wtih i,i-difluoro-2-iodoethane (1.14 mL, 1.92 mmol) and K2C03 (1.6 g, 11.58 mmol)and heated at 60 C overnight, The reaction was diluted with EtOAc and washed with saturated, aqu. NaHCO3, then with brine. The organics were dried over Na2SO4, filtered,and concentrated, The crude material was purified by chromatography on silica (0-30% EtOAc in hexanes) to give the title compound as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17368-12-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20260-53-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

jOZllj To a stirred solution of 4-aminobeuzene-1,3-diol hydrochloride (0.50 g, 3.09 mmol) in pyridine (6 mL) with ice cooling, was added ilicotinoyl chloride hydrochloride (0.55 g, 3.09 mmol) portion-wise. The mixture was stirred at room temperature for 16 hours. The mixiure was concentratci1 in vucuo and the residue was diluted with water (50 mL) and extracted with ethyl aceffite (2 x 60 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by FCC (silica, 30-100% ethyl acetate in heptane) gave the title compound 148 mg (21% yield) as a light brown solid. 6H NMR (250 MHz, DMSO) 9.47 (d, J= 88.0 Hz, 3H), 9.10 (d, J = 1.7 Hz, 1R), 8.73 (dd, J = 4.8, 1.5 Hz, 1H), 8.28 (dt, J = 7.9, 1.9 Hz, 1H), 7.53 (dd, J = 7.7, 5.1 Hz, 1H), 7.20 (d, J = 8.6 Hz, 1H),6.36 (d, I = 2.6 Hz, 1H), 6.24 (dd, J = 8.6, 2.6 Hz, 1H). Tr(METCRI27S) = 0.79 mm, (ESt) (MtH)t 23 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20260-53-1, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem