Butylamine → Phenylmethyl 4-bromo-2-(butylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

Phenylmethyl 4-bromo-2-fluorobenzoate (Example 192, 315 mg, 1.02 mmol) was combined with n-butylamine (110 μl, 1.12 mmol, 1.1 eq.) and solid cesium carbonate (1.66 g, 5.1 mmol, 5.0 eq.) in anhydrous methyl sulfoxide (4 mL) and heated at 75° C. for 1.5 hours. The reaction was cooled and partitioned between diethyl ether and water. The aqueous layer was separated and extracted with fresh ether. The organic layers were combined, washed with brine (4×), dried (MgSO4), and concentrated in vacuo to a crude oil. The crude was purified by flash chromatography on silica gel eluted with 95:5 hexanes/ether to provide the title compound as a yellow oil (52 mg, 14%): 1H NMR (300 MHz, CDCl3) δ7.76 (d, 1 H), 7.71 (broad s, 1 H), 7.41-7.32 (m, 5 H), 6.80 (s, 1 H), 6.63 (d, 1 H), 5.26 (s, 2 H), 3.16-3.10 (m, 2 H), 1.69-1.60 (m, 2 H), 150-1.38 (m, 2 H), 0.95 (t, 3 H); MS m/z 362.0 and 364.0 (MH+ and MH+2).

Provenance & Evidence