Methyl iodide → HCID 42646741, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6,7-dihydro-4-hydroxy-7-isopropyl-N-(3-(4-methylpiperidin-1-yl)propyl)-6-oxothieno[2,3-b]pyridine-5-carboxamide (0.075 g, 0.20 mmol) in THF (2.5 mL) at −78° C. was added n-butyllithium (0.087 mL, 2.5 M in hexanes, 0.22 mmol). The reaction mixture was warmed to 0° C. for 30 min and re-cooled to −78° C.; then methyl iodide (0.037 mL, 0.40 mmol) was added. The mixture was warmed to room temperature, stirred for 4 h and concentrated. The residue was dissolved in dichloromethane; the resulting solution was washed with water, dried over anhydrous sodium sulfate and concentrated to afford the title compound as an off-white solid (0.077 g, 99%). 1H NMR (400 MHz, CD3OD): δ 7.35 (d, 1H), 7.20 (d, 1H), 3.55 (t, 2H), 3.49-3.45 (m, 2H), 3.40 (t, 4H), 3.09 (s, 3H), 2.17-2.09 (m, 2H), 1.91 (m, 4H), 1.76-1.62 (m, 2H), 1.64 (d, 6H); MS: m/e 392 (M+H+).

Provenance & Evidence