Triethylamine → HCID 59751038, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one (630 mg, 3 mmol), thioformamide (30 mL, 30 mmol; described in: J. Med. Chem. 1995, 858-868) and triethylamine (0.42 mL, 3 mmol) in dioxane was heated at 110° C. for 3 h. Additional thioformamide (10 mL, 10 mmol) was added and the reaction was stirred at 110° C. for 2 h. This batch was combined with an new batch starting from 230 mg of 5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one and the combined reaction mixtures was concentrated to approximately 10 mL and an aqueous saturated sodium hydrogencarbonate solution (50 mL) was added and the solution was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated in vacuo. The crude product was purified on a silica gel column using heptane/ethyl acetate, (1:2), as the eluent to give 400 mg (35% yield) of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 10.47 (s, 1 H), 9.15 (s, 1 H), 7.97 (s, 1 H), 7.83 (br s, 2 H), 6.87 (d, J=8 Hz, 1 H), 3.54 (s, 2 H); MS (ES) m/z 217 (M++1).

Provenance & Evidence