1-methyl-2-(tributylstannyl)-1H-pyrrole → 1-[3-(1-methyl-1H-pyrrol-2-yl)phenyl]-N-(Pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide

Participants

Reaction Steps

A mixture of 1-(3-bromophenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (85 mg, 0.209 mmol), Pd(PPh3)2Cl2 (28 mg, 0.040 mmol) and Ag2O (45 mg, 0.196 mmol) was added in one portion to a flask charged with 1-methyl-2-tributylstannanyl-1H-pyrrole (0.391 g, 1.06 mmol). The flask was evacuated and backfilled with N2 (2×) then charged with anhydrous DMF (3.0 mL). After stirring at rt for 5 min the reaction mixture was heated to 90° C. under N2 for 2 d. Later, the reaction was cooled to rt and treated with 1 M aq KF (3 mL) and stirred overnight at rt. Then filtered through Celite (using MeOH to rinse the Celite) and purified by MDPS to provide the product as a white solid. MS (ES+): m/z 408.46 (100) [MH+].

Provenance & Evidence