反应详情

(Ref.: J. Org. Chem. 2002, 67, 6226-6227) 6-Azaindole (2.5 g, 21.25 mmol) is added to a stirred suspension of AlCl3 (11.3 g, 84.5 mmol) in CH2Cl2 (150 mL). After stirring at rt for 1 h, acetyl chloride (6.65 g, 84.5 mmol) is added drop wise and the resulting mixture is stirred for 18 h. The mixture is cooled to 0° C., quenched with MeOH (75 mL) and stirred for 1 h. Silica gel (40 mL), MeOH and DCM are added to the mixture, the solvents are removed under vacuum and the residue is purified by silica gel chromatography eluting with 10% MeOHl in DCM to afford 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (1.52 g, 45%). MS: 161 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.20 (s, 1H), 8.95 (s, H), 7.82(d, 1H), 8.72 (d, 1H), 8.43 (d, 1-H), 2.64(s, 3H).

1. stirringthe resulting mixture is stirred for 18 h
2. temperatureThe mixture is cooled to 0° C.
3. customquenched with MeOH (75 mL)
4. stirringstirred for 1 h
5. additionSilica gel (40 mL), MeOH and DCM are added to the mixture
6. customthe solvents are removed under vacuum
7. customthe residue is purified by silica gel chromatography
8. washeluting with 10% MeOHl in DCM