Sodium Carbonate → 2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(2-bromo-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (10.4 g; 18.5 mmol), potassium hexacyanoferrate trihydrate (1.9 G; 4.49 mmol) and sodium carbonate (2.4 g; 22.6 mmol) was stirred in N,N-dimethylacetamide (32 mL). Palladium acetate was added (0.48 g; 2.13 mmol). The reaction was stirred at 120° C. for 16 hours. The reaction was diluted with diethyl ether and filtered over a pad of silica gel and celite. The mother liquor was washed with water (3×) and brine. It was dried over sodium sulfate and concentrated under reduced pressure. The crude was purified over a 330 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane) to give 8.45 g (89.9%) of title compound as a tan solid. MS (ES+): Calc: 508.3, Found: 509.2 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.76 (s, 1H), 7.75 (d, J=8.30 Hz, 1H), 7.68 (s, 3H), 7.62 (dd, J=8.30 Hz, 1H), 4.96 (s, 2H), 4.89 (s, 2H), 4.22 (s, 3H).

Provenance & Evidence