Diethyl (cyanomethyl)phosphonate → HCID 178437655, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethylphosphonoacetonitrile (15 μL, 0.094 mmol) in THF (1 mL) was cooled to 5° C. in an ice bath and potassium t-butoxide (1 M in THF, 94 μL, 0.094 mmol) was added dropwise. The reaction was stirred at 5° C. for 30 min and a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-2-ethyl-1H-imidazole-5-carboxamide (40 mg, 0.085 mmol) in THF (1 mL) was added dropwise. The reaction was stirred at 5° C. for 30 min, warmed to room temperature and stirred for an additional 60 min. The reaction was quenched with water (1 mL) and concentrated to a yellow oil. The crude material was purified by column chromatography (10% to 100% EtOAc/hexanes gradient) to afford the title compound (32 mg, 76%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.69 (s, 1H), 8.05 (t, 1H), 7.58 (d, 1H), 7.53 (s, 1H), 7.47-7.44 (m, 1H), 7.31 (t, 1H), 7.23 (s, 1H), 7.00 (s, 1H), 6.58 (d, 1H), 4.49 (d, 2H), 2.55 (q, 2H), 1.13 (t, 3H). MS: m/z 493, 495 (M+1).

Provenance & Evidence