Bromochloromethane → HCID 86656549, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 93 (257 mg, 0.517 mmol), HATU (196 mg, 0.517 mmol) and N-methylmorpholine (56.8 μl, 0.517 mmol) in dry DMF (5 ml) is stirred at 70° C. under nitrogen for 1 hour. Further HATU (40 mg, 0.105 mmol) is added and the resulting mixture is stirred at 70° C. for 30 minutes. The solution is cooled to RT and it is poured into a solution of thioacetic acid (74.2 μl, 1.033 mmol) in dry DMF (2 ml). The resulting solution is stirred at RT under nitrogen for 2 hours. Potassium thioacetate (59.0 mg, 0.517 mmol) is added and the mixture is stirred at RT for 2 hours. NaHCO3 (87 mg, 1.033 mmol) and bromochloromethane (101 μl, 1.550 mmol) are added. The resulting mixture is stirred at RT under nitrogen overnight. The reaction mixture is partitioned between AcOEt and brine; the aqueous phase is extracted with AcOEt and the combined organic layers are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated and the crude is purified by silica gel chromatography (AcOEt/petroleum ether 3/7) to give a solid which is further triturated with petroleum ether to afford the title compound (32 mg, 10.9%).

Provenance & Evidence