Methyl iodide → HCID 118235741, compound

Participants

Reaction Steps

A solution of Example 43 (1 g, 1.97 mmol) and methyl iodide (0.25 mL, 4.1 mmol) in THF (10 mL) was cooled under nitrogen to −78° C. and 1M lithium hexamethyldisilazane solution (8.0 mL, 8 mmol) was added dropwise. The mixture was left stirring overnight, allowing the temperature to rise slowly to ambient temperature. The reaction mixture was partitioned between EtOAc and brine. The organic layer was washed once with brine, dried over MgSO4, filtered and concentrated in vacuo, then purified by column chromatography on SiO2, eluting with EtOAc-hexane (4:1 v/v). The residue was crystallised from diethyl ether/hexane, filtered, and washed with diethyl ether/hexane, then dried, to give the title compound (0.26 g, 25%) as a white solid. δH (400 MHz, DMSO-d6) 8.63 (m, 2H), 8.35 (m, 1H), 7.56 (dd, J 7.6, 1.5 Hz, 1H), 7.50 (m, 1H), 7.43 (m, 1H), 7.34 (m, 1H), 7.28 (m, 1H), 7.16 (d, J 7.9 Hz, 1H), 7.12 (t, J 72, 76 Hz, 1H), 4.96 (m, 1H), 4.25 (m, 2H), 3.66 (s, 3H), 3.34 (m, 2H), 2.27 (s, 3H), 2.03 (m, 2H), 1.72 (d, J 7.3 Hz, 3H), 1.44 (m, 2H), 1.23 (m, 3H). LCMS (pH 10): MH+ 536, RT 2.31 minutes.

Provenance & Evidence