74% |
With sodium hydroxide; In ethanol; at 90℃; for 18h; |
<strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> (120mg, 0.84mmol) was dissolved in ethanol (10ml). 6N Sodium hydroxide (1.4ml, 8.4mmol) was added, and the mixture was stirred for 18 hours at 90. The mixture was distilled under reduced pressure, and then 1N hydrochloric acid solution was added. The resulting solution was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (100mg, 74%). [945] NMR:1H-NMR(400HMz, DMS)-d 6); delta 12.08(brs, 1H),8.11(d, 1H), 7.83(d, 1H), 7.70(d, 1H), 6.58(d, 1H) |
|
|
b) 1 H-Pyrrolo[2,3-b]pyridine-6-carboxylic acid; A suspension of 1 H-pyrrolo[2,3-b]pyridine-6-carbonitrile (690 mg, 4.82 mmol) in NaOH 2M (12 ml) was stirred at 100 C for 6 h. The reaction mixture was washed with diethyl ether and the aq. phase was set slightly acidic (pH 6-7) with cone. HCI. The solid formed was filtered off and dried to provide the title compound.LC-MS: RtH8= 0.51 min. (100% purity, ESI+ 163);1H-NMR (400 MHz, DMSO-D6): delta 12.78 (s, 1 H), 12.01 (s, 1 H), 8.08 (d, 1 H), 7.80 (m, 1 H), 7.73 (s, broad, unresolved, 1 H), 6.56 (s, broad, 1 H). |
176 g |
With sodium hydroxide; In ethanol; at 80℃; |
With 5 liters three bottles,Under mechanical agitation,123 g of <strong>[189882-33-5]6-cyano-7-azaindole</strong> was added to 1.7 liters of ethanol,At room temperature,Add the concentration of 5N sodium hydroxide solution 1.2 liters,The temperature was kept at 80 C overnight,Thin layer chromatography TLC detection,To the raw material reaction completely,The reaction was stopped. Post-processing:After naturally dropping to room temperature, the reaction solution was poured into 5 liters of ice water and the pH was adjusted to 3 to 4 with hydrochloric acid to precipitate solidBody products, filtration, drying,be made of7-azaindole 6-carboxylic acid176 g.Sampling detection,High Pressure LiquidThe purity was 97%. |