Cesium carbonate → HCID 59393681, compound

Participants

Reaction Conditions

Reaction Steps

Chloromethyl methyl sulfide (12.0 μL, 0.140 mmol) was added to a stirred suspension of 6a (42.0 mg, 0.0910 mmol) and cesium carbonate (46.0 mg, 0.140 mmol) in DMF (2.00 mL) at rt, and the resulting mixture was heated at 40° C. for approximately 2 h. The reaction mixture was cooled to rt, and second portions of cesium carbonate (46.0 mg, 0.140 mmol) and chloromethyl methyl sulfide (12.0 μL, 0.140 mmol) were added. The resulting mixture was heated at 40° C. for about another 3 h. After cooling to rt, the reaction mixture was poured into 10% aqueous sodium hydrosulfate and extracted three times with diethyl ether. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 20%-50% EtOAc/hexanes as eluent) afforded the title compound 6b. m/z (ES) 525 (MH)+ 1HNMR (500 MHz, CDCl3): δ 9.28 (d, 1H, J=2.1 Hz), 8.51 (br, 1H), 8.45 (dd, 1H, J=2.4, 8.3 Hz), 8.32 (br, 1H), 8.07 (d, 1H, J=8.9 Hz), 7.92 (d, 1H, J=9.0 Hz), 7.55 (m, 6H), 5.25 (s, 2H), 3.21 (m, 1H), 2.28 (s, 3H), 1.81 (s, 3H), 0.93 (d, 3H, J=6.4 Hz), 0.89 (d, 3H, J=6.6 Hz).

Provenance & Evidence