Sodium Carbonate → 3-cyclohexyl-N-[(dimethylamino)sulfonyl]-2-(2-formylphenyl)-1H-indole-6-carboxamide

Participants

Reaction Steps

A mixture of 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide (950 mg, 2.22 mmol), LiCl (370 mg, 4.44 mmol), tetrakis(triphenylphosphine)palladium(0) (130 mg, 0.11 mmol) in toluene (30 mL) and ethanol (30 mL) containing aqueous 1 N Na2CO3 (15 mL, 15 mmol) was stirred under reflux for 18 hr. The mixture was diluted with ethyl acetate and washed with 1 N HCl (3×) followed by brine (3×). The solution was dried over Na2SO4 and concentrated to dryness to afford the titled compound as a yellow solid (1.06 g, 106%) which contained some triphenyl oxide. The product was used in the following step without additional purification. MS m/z 454 (MH+).

Provenance & Evidence