Ammonium Chloride → HCID 52933299, compound

Participants

Reaction Conditions

Reaction Steps

To 3-iodo-5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (5, 0.49 g, 1.14 mmol) in 6.8 mL of tetrahydrofuran at −50° C. under nitrogen, isopropylmagnesium chloride (0.569 mL, 2.0 M in tetrahydrofuran, 1.14 mmol) was added slowly. The reaction was allowed to warm to 5° C. over 70 minutes, then cooled to −60° C. and (2-chloro-benzyl)-(6-fluoro-5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (48, 0.23 g, 0.63 mmol) in 30.0 mL of tetrahydrofuran was added. The reaction was allowed to warm to room temperature over 1 hour, then poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound as a white solid (176, 0.400 g). MS (ESI) [M+H+]+=669.4.

Provenance & Evidence