Potassium Carbonate → (4-bromo-1H-indol-2-yl)(pyrrolidin-1-yl)methanone

Participants

Reaction Steps

Step 2 A solution of N-(3-bromo-2-methylphenyl)-1H-imidazole-2-carboxamide (0.70 g, 2.499 mmol) in DMF (12.5 mL) was treated with potassium carbonate (0.794 g, 5.75 mmol) and 2-bromo-1,1-diethoxyethane (0.395 mL, 2.62 and the mixture was stirred at rt. After 18.25 h, the mixture was diluted with EtOAc, filtered to remove some tan solid, and washed sequentially with 1 M hydrochloric acid and NaHCO3 (aq), and dried and concentrated to provide (4-bromo-1H-indol-2-yl)(pyrrolidin-1-yl)methanone as a tan solid (205 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 11.96 (s, 1 H) 7.46 (d, J=7.9 Hz, 1 H) 7.27 (d, J=7.5 Hz, 1 H) 7.06-7.17 (m, 1 H) 6.82 (s, 1 H) 3.85 (t, J=6.8 Hz, 2 H) 3.55 (t, J=6.8 Hz, 2 H) 1.93-2.04 (m, 2 H) 1.81-1.92 (m, 2 H). Mass spectrum m/z 293, 295 (M+H)+.

Provenance & Evidence