Category: 75291-85-9

Application of 75291-85-9, 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.75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, molecular weight is 235.47, as common compound, the synthetic route is as follows.

B) 2-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)nicotinamide, bis(trifluoroacetic acid) salt; 4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (51.7 mg, 0.21 mmol) and 5-bromo-2-chloronicotinamide (50 mg, 0.21 mmol) were suspended in 3:1 isopropanol-NMP (2.1 mL). 4N HCl in 1,4-dioxane (0.21 mL, 0.84 mmol) was added and the reaction was heated to 100 C. for 240 h. The isopropanol was removed by rotary evaporation and the resulting residue was partitioned between 5% aq. NaHCO3 solution (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer was extracted EtOAc (2×10 mL). The combined organic layers were washed with 10% LiCl (20 mL), dried (MgSO4) and concentrated. The crude product was purified by preparative (RP) HPLC chromatography (YMC S5 ODS, 30×75 mm, 10 minute gradient from 33% to 90% aqueous methanol with 0.1% TFA, 40 mL/min). The fractions containing the desired product were combined and concentrated to afford the desired product as a tan powder (10.1 mg, >98% HPLC purity). 1H NMR (DMSO-d6) delta 12.00 (s, 1H), 11.38 (s, 1H), 8.44 (s, 1H), 8.44 (dd, 1H, J=23.91, 2.03 Hz), 8.13 (d, 1H, J=5.59 Hz), 8.06 (d, 1H, J=13.23 Hz), 7.92 (s, 1H), 7.42 (s, 1H), 7.29-7.38 (m, 2H), 6.46 (d, 1H, J=5.59 Hz), 6.32 (s, 1H); MS(ESI+) m/z 442.1 (M+H)+.

Statistics shows that 75291-85-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloronicotinamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78140; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75291-85-9 , The common heterocyclic compound, 75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7%).; The title compound was prepared using 5-bromo-2-chloronicotinamide (1.50 g, 6.37 mmol), tert-butyl piperazine 1-carboxylate (1.19 g, 6.37 mmol) and potassium carbonate (3.52 g, 25.48 mmol) in acetonitrile (20 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (2.25 g, 91.8%).MS (ESI, pos. ion) m/z: 385.2 [M+H] and?H NMR (400 IVIFIz, DMSO-d6): (ppm) 8.31 (d, J= 2.4 Hz, 1H), 7.95 (s, 1H), 7.82 (d, J= 2.0 Hz, 1H), 7.63 (s, 1H), 3.42 (d, J= 4.8 Hz, 4H), 3.27 (d, J= 4.8 Hz, 4H), 1.41 (s, 9H).

The synthetic route of 75291-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; LIANG, Haiping; YI, Chao; ZHANG, Ji; (94 pag.)WO2016/192657; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 75291-85-9, name is 5-Bromo-2-chloronicotinamide. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Bromo-2-chloronicotinamide

Preparation 118tert-butyl (3S,4R)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl-(3S,4R)-3-fluoro-4-hydroxy-piperidine- 1 -carboxylate (WO 20131011402 Al), 3.5 g, 15.98 mmol) in DMSO (20 mL) was added potassium tert-butoxide(2.68 g, 23.97 mmol) and the mixture was stirred at room temperature for 30 minutes. 5-bromo-2-chloropyridine-3-carboxamide (Preparation 177, 2.75 g, 15.98 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction was quenched by the addition of water (20 mL) and extracted into EtOAc (2 x 100 mL). The organic layers were combined, washed with water (2 x 50 mL), dried over sodium sulphate and concentrated in vacuo. Theresidue was purified using silica gel column chromatography eluting with 20% EtOAc inheptanes to afford the title compound (5.00 g, 75%).1H NMR (400 MHz, DMSO-d6): O ppm 1.40 (5, 9H), 1.80-1.86 (m, 1H), 1.92-1.97 (m, 1H), 2.93-3.00 (m, 1H), 3.07-3.12 (m, 1H), 3.90-4.18 (m, 2H), 4.95-5.08 (m, 1H), 5.35-5.43 (m, 1H), 7.52(br 5, 1 H), 7.92 (br 5, 1 H), 8.27 (d, 1 H), 8.43 (d, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 75291-85-9.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75291-85-9, 5-Bromo-2-chloronicotinamide, 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, 75291-85-9, blongs to pyridine-derivatives compound. SDS of cas: 75291-85-9

Preparation 133(35,45)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine- 1 -carboxylate (WO 20131011402 Al, 605 mg, 2.76 mmol) in DMSO (4 mL) was added potassium tert-butoxide (464 mg, 4.14 mmol) and the mixture stirred at room temperature for 30 minutes. 5-bromo-2- chloronicotinamide (Preparation 177, 650 mg, 2.76 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction was quenched by the addition of water andextracted into EtOAc. The organic layer was collected, washed with water, dried over sodiumsulphate and concentrated in vacuo. The residue was purified using silica gel columnchromatography eluting with 30% EtOAc in heptanes to afford the title compound (800 mg,69%).1H NMR (400 MHz, DMSO-d6): O ppm 1.41 (5, 9H), 1.74 (m, 1H), 2.06 (m, 1H), 3.28-3.83 (m,4H), 4.80-4.93 (m, 1H), 5.41 (m, 1H), 7.64 (br 5, 1H), 7.68-7.82 (m, 2H), 8.21 (m, 1H), 8.42 (5,1H).MS mlz 318 [M79Br-Boc+H]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75291-85-9, its application will become more common.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75291-85-9 ,Some common heterocyclic compound, 75291-85-9, molecular formula is C6H4BrClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Preparation 119tert-butyl (3R,4S)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate A solution of 5-bromo-2-chloronicotinamide (Preparation 177, 11.7 g, 49.8 mmol), tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1 -carboxylate (WO 20131011402 Al, 10.9 g, 49.8 mmol) and potassium tert-butoxide (6.72 g, 60 mmol) in DMSO (165 mL) was stirred at roomtemperature for 16 hours. The reaction was quenched by the addition of water (500 mL) and extracted into EtOAc (3 x 500 mL). The organic layers were combined, concentrated in vacuo and the residue triturated with diethylether to afford the title compound as a pale yellow powder(17.8 g, 85%).1H NMR (400 MHz, DMSO-d6): O ppm 1.39 (5, 9H), 1.82 (m, 1H), 1.94 (m, 1H), 3.01 (m, 1H),3.27 (m, 1H), 3.93 (5, 1H), 4.14 (5, 1H), 4.98 (d, 1H), 5.38 (dddd, 1H), 7.51 (5, 1H), 7.90 (5, 1H),8.26 (d, 1H), 8.41 (d, 1H). MS mlz 418 [M79Br-fH]

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 75291-85-9, 5-Bromo-2-chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem