Methyl iodide → HCID 57429429, compound

Participants

Reaction Steps

A mixture of 2-(4-(1-hydroxypropan-2-yl)phenyl)-6-methoxyisoindolin-1-one (0.042 g, 0.14 mmol), silver oxide (0.196 g, 0.42 mmol), iodomethane (0.070 mL) and 4 Å molecular sieves (0.050 g) in acetonitrile (2 mL) was stirred for 96 h at room temperature. After this time, the mixture was diluted with water (10 mL) and ethyl acetate (10 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an off-white solid Purification by flash chromatography (silica, 1:1 ethyl acetate/hexanes) afforded 6-methoxy-2-(4-(1-methoxypropan-2-yl)phenyl)isoindolin-1-one (0.031 g, 72%) as a white solid: mp 116-118° C.; 1H NMR (300 MHz, CDCl3) δ 7.78 (dd, J=8.7, 2.0 Hz, 2H), 7.40-7.38 (m, 2H), 7.29 (dd, J=8.6, 1.9 Hz, 2H), 7.15 (dd, J=8.3, 2.4 Hz, 1H), 4.78 (m, 2H), 3.89 (s, 3H), 3.55-3.41 (m, 2H), 3.34 (s, 3H), 3.04 (q, J=7.0 Hz, 1H), 1.29 (d, J=7.0 Hz, 3H); ESI MS m/z 312 [M+H]+.

Provenance & Evidence