3-Nitrophenylboronic Acid → 3,3-Dimethyl-1,3-dihydro-indol-2-one

Participants

Reaction Steps

Using the standard coupling conditions given in Example 1, the title compound was prepared from 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole (0.25 g, 1.1 mmol), tetrakis(triphenylphosphine) palladium (0.08 g, 0.07 mmol) in dimethoxyethane (5 mL) with 3-nitrophenylboronic acid (0.22 g, 1.3 mmol) and sodium carbonate (0.35 g, 3.3 mmol) in 5 mL water. The title compound (0.17 g, 60%) was obtained as a brown semi-solid: 1H NMR (CDCl3)δ 1.38 (s, 3H), 3.40 (s, 2H), 6.72 (d,J=8.0 Hz, 1H), 7.29-7.34 (m, 2H), 7.54 (dd,J=8.0, 8.0 Hz, 1H), 7.86 (d,J=7.8 Hz, 1H), 8.09 (dd,J=8.0, 1.5 Hz, 1H), 8.40 (dd,J=2.0, 2.0 Hz, 1H); 13C-NMR (CDCl3)δ 27.89 (q), 41.93 (s), 62.05 (d), 109.78, 120.87, 121.02, 121.23, 126.87 (d), 129.19 (s), 129.69, 132.52 (d), 139.64, 143.75, 148.94, 151.17 (s); MS (EI) m/z 268 (M)+.

Provenance & Evidence