Boron tribromide → HCID 178432959, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 ml round bottom flask containing −78° C. solution of 2-(4-cyclopropylphenyl)-N-[(4-methoxyphenyl)(2-methyl-1H-imidazol-4-yl)methyl]acetamide (80.00 mg, 0.213 mmol) in 2.0 ml of CH2Cl2 was added drop-wise 1.0 N BBr3 in CH2Cl2 (1.065 ml, 1.065 mmol). The resulting solution was stirred at −10° C. for 2 hours. The reaction mixture was quenched with diethyl ether. Water was added and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (10-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 15.20 mg (20%) of the title compound. 1H NMR (CD3OD, 400 MHz) δ 7.136 (m, 4H), 7.012 (m, 2H), 6.938 (d, J=1.10 Hz, 1H), 6.797 (m, 2H), 6.067 (s, 1H), 3.523 (s, 2H), 3.344 (s, 1H), 2.552 (s, 3H), 1.868 (m, 1H), 0.932 (m, 2H), 0.635 (m, 2H). ES-MS [M+1]+: 362.3.

Provenance & Evidence