Methyl iodide → HCID 71625034, compound

Participants

Reaction Steps

Compound 7 (200 mg, 0.6 mmol) was added in portions to a mixture of sodium hydride (60 mg, 1.2 mmol) in DMF (5 mL) at 0° C. After 15 min, methyl iodide (50 μL, 0.9 mmol) was added and the mixture was stirred for 1 h. The reaction was allowed to warm to rt and stirred overnight under N2. The reaction mixture was then quenched with ice water and extracted with EtOAc. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 50% EtOAc-hexanes to provide 166 mg (63%) of product 4 as an off white solid, mp 110-111° C. 1H NMR (300 MHz, DMSO-d6) δ 2.35 (s, 3H), 3.83 (s, 3H), 4.00 (s, 3H), 7.06 (d, J=9 Hz, 2H), 7.23-7.29 (m, 4H), 7.63 (d, J=9 Hz, 1H). LC-MS (CI): m/z 346.1 [(M+H)+ C18H16ClNO2S requires 345.06]. Purity (100%). Calcd for C18H16ClNO2S: C, 62.51; H, 4.66; N, 4.05; S, 9.27; Cl, 10.25. Found: C, 62.79; H, 4.64; N, 3.98; S, 9.05; Cl, 10.03.

Provenance & Evidence