Diazomethane → 2-Diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone

Participants

Reaction Steps

To a solution of 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride (395) (1.2 g, 8.83 mmol) in tetrahydrofuran (80 mL) was dropwise added a solution of diazomethane [which was freshly synthesized following the standard procedure, starting from methylurea via formation of NMU and followed by KOH treatment] in ether (80 mL) at −5° C., while stirring very slowly. The reaction mixture was left standing for 1 h at 0° C. (TLC, 30% ethyl acetate in hexane, Rf=0.6). Volatiles were removed to get the crude product which was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 2-diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone (396) (1.1 g, 90%) as a yellow sticky solid.

Provenance & Evidence