Azide → HCID 86696504, compound

Participants

Reaction Steps

To a solution of 2-azido-N-(3-phenylpropyl)-3-(trifluoromethyl)pyridin-4-amine (125 mg, 0.389 mmol) in tetrahydrofuran (4.0 mL) and water (0.066 mL, 3.69 mmol was added trimethylphosphine (1.0 M in tetrahydrofuran; 0.443 mL, 0.443 mmol. After four hours starting material remained and an additional 500 μL of trimethylphosphine was added. After 21 hours, LC/MS showed a 6.7:1 ratio of desired:starting material. An additional 200 μL of trimethylphosphine was added. After 25 hours the ratio by LC/MS was 12:1 product:starting material. After 27 hours the mixture was concentrated. This material was purified on silica gel (12 g) equilibrated in hexane, loaded in dichloromethane and eluted using hexane (96 mL), 20% EtOAc/hexane (250 mL), 20 to 50% EtOAc/hexane (320 mL, linear gradient). Fractions 39-50 gave 84.5 mg of an off white crystalline solid. This was consistent with desired product by 1H NMR containing 10% of the starting azide. The material was used as is. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.79 (d, J=6.0 Hz, 1H), 7.39-7.29 (m, 2H), 7.25-7.15 (m, 3H), 5.98 (d, J=6.0 Hz, 1H), 4.96 (br. s., 3H), 3.25-3.12 (m, 2H), 2.73 (t, J=7.5 Hz, 2H), 1.98 (quin, J=7.3 Hz, 2H).

Provenance & Evidence