p-Toluenesulfonic acid → HCID 66740907, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2-(3,4-dimethoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-carbaldehyde (280 mg, 0.76 mmol), 2-chloro-6-fluoroaniline (332 mg, 2.28 mmol), TsOH (72 mg, 0.38 mmol) in THF (8 mL) was heated at reflux for 15 h over molecular sieves (4A). The solution was cooled to 0° C., and NaBH4 (57 mg, 1.5 2 mmol) was added in several portions. The resulting mixture was stirring for 1 h, and filtered through Celite™ to remove molecular sieves. The filtrate was quenched with H2O (5 mL), 2N NaOH (5 mL) and extracted with DCM (2×10 mL). The organic layers were dried over MgSO4 and concentrated to give a residue, which was purified by flash chromatography to provide the title compound as a white solid (157 mg, 0.315 mmol, 42%). 1H NMR (400 MHz, CDCl3) δ1.49 (s, 6H), 3.72 (s, 3H), 3.85 (s, 3H), 4.13 (d, 2H), 4.65 (br, 1H), 6.45 (dd, 1H), 6.48 (m, 2H), 6.51 (d, 1H), 6.60 (m, 1H), 6.64 (d, 1H), 6.76 (dd, 1H), 6.80 (t, 2H), 7.00 (dt, 1H), 7.13 (s, 1H). MS (EI) m/z 498 [M+H]+.

Provenance & Evidence