Methyl iodide → HCID 67582419, compound

Participants

Reaction Steps

Sodium hydride, 60% dispersion in oil (0.57 g, 14 mmol) was added portionwise to a suspension of (E)-4-(indol-5-yl)ethenylpyridine (2.82 g, 12.8 mmol) [prepared from 4-vinylpyridine and 5-bromoindole by an analogous procedure to Example 16] in dimethylformamide (100 ml). The mixture was stirred at room temperature, under nitrogen, for 1.5 h to give a red solution which was then cooled to 0° C. and treated dropwise with methyl iodide (0.88 ml, 14 mmol). The reaction mixture was stirred at 0° C. under nitrogen for 10 min, allowed to warm to room temperature and stirred for a further 30 min. The resulting suspension was diluted with water (200 ml), the solid collected under suction, washed with 5% aqueous sodium sulfite solution then water and dried in vacuo to afford the title compound as a buff solid (3.07 g); δH (CDCl3) 3.81 (3H, s, N-CH3), 6.51 (1H, dd, J 3.1, 0.7 Hz, 3'-H), 6.98 (1H, d, J 16.3 Hz, CH=CH), 7.07 (1H, d, J 3.1 Hz, 2'-H), 7.31-7.51 (5H, m, CH=CH, ArH), 7.78 (1H, d, J 1.4 Hz, 4'-H), 8.55 (2H, m, 2-H, 6-H-1).

Provenance & Evidence