Category: 144657-66-9

Synthetic Route of 144657-66-9, 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. 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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.

A solution of tert-butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (420 mg, 1.71 mmol) in ethanol (10 mL) was cooled to 0 C with stirring under nitrogen before sodium borohydride (126.6 mg, 3.35 mmol) was added. The reaction mixture was allowed to warm to rt and stirred for 1.25 h.An aqueous solution of hydrochloric acid (2 M, 4 drops) was added, followed immediately by a saturated solution of sodium bicarbonate (1 mL). The reaction mixture was concentrated in vacuo and the residue partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The phases were separated and the aqueous phase further extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, filtered through a cartridgecontaining a hydrophobic frit and the solvent evaporated in vacuo. The residue was dissolved in a1:1 mixture of dichloromethane/methanol (10 mL), concentrated under a stream of nitrogen, anddried in vacuoto give a white solid which was dissolved in dichloromethane (5 mL) and loaded ontoa 25 g SNAP silica cartridge which was purified by flash chromatography, eluting wih a gradient ofSO-100% ethyl acetate in cyclohexane. The required fractions were concentrated in vacuo beforebeing dissolved in a 1:1 mixture of dichloromethane/methanol (10 mL), transferrred to a tarred vial,concentrated under a stream of nitrogen and dried in vacuo to give a white solid; tert-butyl 3- (hydroxymethyl)-1 H-pyrrolo[2,3-b] pyrid me- 1-carboxylate (199.7 mg, 0.80 mmol, 47 % yield).LCMS (2 mm formic) Rt = 0.72 mi m/z= 249 for [MH]

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 144657-66-9, tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144657-66-9 , The common heterocyclic compound, 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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.

To a solution of isopropylamine (0.52 mL , 6.09 mmol) was added l-(tert- butoxycarbonyl)-3-formyl-7-azaindole (1.50 g, 6.09 mmol) in 10 mL MeOH. The solution was stirred at ambient temperature for 2h. Sodium borohydride (576 mg, 15.2 mmol) was added, and the reaction mixture was stirred for 16h at ambient temperature. The mixture was concentrated and partitioned between 10% K2CO3 and ether. The organics were washed with water and brine, then dried over Na2S04, filtered and concentrated. The crude product was carried on to the next step. LCMS [M+H]+ = 190.2.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn, J.; EGBERTSON, Melissa; BRNARDIC, Edward; JONES, Kristen; SANDERS, John, M.; HENZE, Darrell, A.; WO2013/176970; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 144657-66-9 , The common heterocyclic compound, 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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.

To a solution of isopropylamine (0.52 mL , 6.09 mmol) was added l-(tert- butoxycarbonyl)-3-formyl-7-azaindole (1.50 g, 6.09 mmol) in 10 mL MeOH. The solution was stirred at ambient temperature for 2h. Sodium borohydride (576 mg, 15.2 mmol) was added, and the reaction mixture was stirred for 16h at ambient temperature. The mixture was concentrated and partitioned between 10% K2CO3 and ether. The organics were washed with water and brine, then dried over Na2S04, filtered and concentrated. The crude product was carried on to the next step. LCMS [M+H]+ = 190.2.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn, J.; EGBERTSON, Melissa; BRNARDIC, Edward; JONES, Kristen; SANDERS, John, M.; HENZE, Darrell, A.; WO2013/176970; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 144657-66-9, 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. 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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.

A mixture of l-(fer?-butyloxycarbonyl)-3-formyl-7-azaindole (Int-16, 9.8 g, 40 mmol) and sodium borohydride (1.7 g, 44 mmol) in methanol (50 mL) were stirred at rt for 4 h. TLC showed the reaction was complete. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, brine, dried, concentrated, and purified by flash column chromatography to afford alcohol Int-17 (8.4 g, 85%).

According to the analysis of related databases, 144657-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCEPION PHARMACEUTICALS, INC.; JIANG, Shan; XING, Xinglong; WANG, Qishan; KONG, Ren; WO2011/23081; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144657-66-9, tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, 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, Quality Control of tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, blongs to pyridine-derivatives compound. Quality Control of tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

General procedure: To a solution of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride in ethanol was added triethylamine and the mixture was stirred at 70 C for 5 min. To the resulting yellow solution were added an aldehyde and a solution of an imine in ethanol. The reaction mixture was stirred in a sealed tube at 50 – 70 C for 18 – 120 h. The reaction mixture was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel or precipitation.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144657-66-9, tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, 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, SDS of cas: 144657-66-9, blongs to pyridine-derivatives compound. SDS of cas: 144657-66-9

To a solution of 1-(tert-butoxycarbonyl)-3-formyl-7-azaindole (2.5g, 10.2 mmol) in 16 mL EtOH was added NaBH4 (115mg, 3.05 mmol). The reaction was stirred at ambient temperature for 4h, concentrated and triturated with IN NaOH. The basic solution was extracted with ether and ethylacetate. The organics were washed with water and brine, then dried over Na2S04, filtered and concentrated. The filtrate was concentrated and purified by silica gel chromatography (50% ethylacetate/hexanes) to give tert-butyl 3-(hydroxymethyl)-lH- pyrrolo[2,3-b]pyridine-l-carboxylate (44%). LCMS [M-tert-Bu]+ = 191.1.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn, J.; EGBERTSON, Melissa; BRNARDIC, Edward; JONES, Kristen; SANDERS, John, M.; HENZE, Darrell, A.; WO2013/176970; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem