Water → HCID 59129243, compound

Participants

Reaction Steps

Freshly recrystallized N-bromosuccinimide (0.278 g, 1.56 mmol) was added portionwise to a solution of 1-(benzo[d][1,3]-dioxol-5-yl)-N-(1H-indol-5-yl)cyclopropanecarboxamide (0.500 g, 1.56 mmol) in N,N-dimethylformamide (2 mL) over 2 minutes. The reaction mixture was protected from light and was stirred bar for 5 minutes. The resulting green solution was poured into 40 mL of water. The grey precipitate which formed was filtered and washed with water to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-1H-indol-5-yl)cyclopropanecarboxamide (0.564 g, 91%). ESI-MS m/z calc. 398.0, found 399.3(M+1)+. Retention time of 3.38 minutes. 1 H NMR (400 MHz, DMSO-d6) 11.37(s, 1H), 8.71(s, 1H), 7.67(d, J=1.8 Hz, 1H), 7.50(d, J 2.6 Hz, 1H), 7.29(d, J=8.8 Hz, 1H), 7.22(dd, J=2.0, 8.8 Hz, 1H), 7.02(d, J=1.6 Hz, 1H), 6.96-6.88(m, 2H), 6.03(s, 2H), 1.43-1.40(m, 2H), 1.09-1.04(m, 2H).

Provenance & Evidence