methyl 2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate synthesis
- Product Name:methyl 2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate
- CAS Number:954215-11-3
- Molecular formula:C11H9BrN2O4
- Molecular Weight:313.1
![1H-Pyrrolo[2,3-c]pyridine, 7-broMo-4-Methoxy-](/CAS/GIF/619331-35-0.gif)
Yield:954215-11-3 99%
Reaction Conditions:
Stage #1: monomethyl oxalyl chloride;7-bromo-4-methoxy-6-azaindole;aluminum (III) chloride in nitromethane;dichloromethane at 20; for 1 h;
Stage #2: with ammonia;water in nitromethane;dichloromethane;
Steps:
5.E2 Methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate
E2 Methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate To a solution of AlCl3 (0.587 g, 4.40 mmol) in DCM-MeNO2 (4:1, 3 mL) was added a solution of 7-bromo-4-methoxy-6-azaindole (0.100 g, 0.440 mmol) in DCM-MeNO2 (4:1, 1 mL), followed by methyl oxalyl chloride (0.162 mL, 1.76 mmol). The resulting deep orange solution was stirred at room temperature for 1 h and then it was quenched by the slow addition of 1M NH4OH. The mixture was extracted with ethyl acetate (2*) and the combined organic phases were dried (MgSO4) and evaporated to give the title compound (0.136 g, 99%) as a white solid weighing: 1H-NMR (400 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.41 (d, J=3.0 Hz, 1H), 7.84 (s, 1H), 3.92 (s, 3H), 3.86 (s, 3H).
References:
US2007/249624,2007,A1 Location in patent:Page/Page column 25-26
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91579-92-9
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1421517-98-7
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1421517-99-8
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