Benzylamine → HCID 57529003, compound

Participants

Reaction Conditions

Reaction Steps

A dried flask was charged with palladium acetate (25.2 mg, 0.11 mmol, 5 mol %), BINAP (104.9 mg, 0.17 mmol, 7.5 mol %), and cesium carbonate (1.46 g, 4.49 mmol). To this mixture was added a solution of ethyl ((1S)-5-{2-[2-(3-bromo-4-methylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (1.12 g, 2.25 mmol) and benzyl amine (0.48 g, 4.49 mmol) in toluene (50 mL) using an addition funnel. The first 15 mL was added quickly (5 minutes) and the remainder added over a period of 1 h. The mixture warmed to 85° C. after the first 30% portion was added. The reaction mixture was stirred at 85° C. for 16 h. The crude was cooled to rt, diluted with ethyl acetate, and then filtered through a Celite® plug. The filtrate was then concentrated under reduced pressure and the residue purified by silica gel flash chromatography (10-20% ethyl acetate in hexanes) to afford 1.1 g (93.3% yield) of desired product. 1H NMR (300 MHz/CDCl3) δ 7.28-7.44 (m, 7H), 7.12 (d, 1H), 7.03 (d, 1H), 6.77 (s, 1H), 6.71 (d, 1H), 4.44 (s, 2H), 4.13-4.22 (m, 4H), 3.82 (br, 1H), 3.51 (qr, 1H), 2.96 (t, 2H), 2.77-2.92 (m, 2H), 2.71 (dd, 1H), 2.31-2.43 (m, 5H), 2.17 (s, 3H), 1.61-1.79 (m, 1H), 1.26 (t, 3H). EI-LCMS(rel abundance), m/z 525.4 (MH+, 100%).

Provenance & Evidence