Benzoyl chloride, 3,4,5-trimethoxy- → (6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone

Participants

Reaction Steps

Ethylmagnesium bromide (3.0 M solution in diethyl ether, 0.43 mL) was added to a mixture of 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.127 g, 0.969 mmol) and anhydrous zinc chloride (0.263 g, 1.94 mmol) in dry CH2Cl2 (20 mL) over 10 min at room temperature. The suspension was stirred for 1 h and then a solution of 3,4,5-trimethoxybenzoyl chloride (0.335 g, 1.45 mmol) in dry CH2Cl2 (10 mL) was added dropwise over 5 min. After 1 h, aluminum chloride (0.129 g, 0.969 mmol) was added. The resulting thick mixture was vigorously stirred for 5 h. The reaction was quenched with water (10 mL) and extracted with CH2Cl2 (20 mL). The organic layer was dried over anhydrous MgSO4 and concentrated to give a brown oil, which was further purified on a silica gel column (MeOH:CH2Cl2=1:25) to give compound 8 (0.150 g, 48%) as a white solid.

Provenance & Evidence