1-(Bromomethyl)-4-(trifluoromethoxy)benzene → HCID 67490680, compound

Participants

Reaction Steps

The major diastereomer of methyl N-(4-{1-[1-(4-chlorophenyl)-2-hydroxyethyl]butyl}benzoyl)-β-alaninate (EXAMPLE 86, Step C, 80 mg, 0.19 mmol), 1-(bromomethyl)-4-(trifluoromethoxy)benzene (97 mg, 0.38 mmol) and Ag2O (87 mg, 0.38 mmol) in DCM (20 mL) was refluxed overnight. After cooling to room temperature, the mixture was filtered, then the filtrate was concentrated. The resulting residue was purified by PTLC to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=8 Hz, 2H); 7.22-7.31 (m, 6H); 7.05-7.12 (m, 4H); 6.90 (t, J=5.4 Hz, 1H); 4.10-4.24 (m, 2H); 332-3.77 (m, 5H); 3.22-3.29 (m, 2H); 2.94-2.98 (m, 2H); 2.67 (t, J=53 Hz, 2H); 1.32-1.44 (m, 2H); 0.88-0.94 (m, 2H); 0.65 (1, J=7.2 Hz, 3H). MS (M+H)+ 592.

Provenance & Evidence