Sodium Carbonate → HCID 16072742, compound

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (207 mg, 0.18 mmol) was added to a stirred and degassed mixture of methyl 2-bromo-1-(2-cyanoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (695 mg, 1.8 mmol), 2-formylphenyl boronic acid (233 mg, 1.56 mmol), LiCl (151 mg, 3.57 mmol) in ethanol (5.8 mL) and toluene (5.8 mL) containing 1M aqueous sodium carbonate (5 mL, 5 mmol). The mixture was stirred under reflux for 2 hr. The mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water (2×), followed by brine, and dried over sodium sulfate. The extract was concentrated and partially purified by chromatography on SiO2 (35 g) using the flash technique and eluting with methylene chloride with between 10-20% ethyl. acetate. A solution of the residue when stood in methanol deposited yellow needles of the titled compound. MS m/z 397 (MH+); (500 MHz, CHLOROFORM-D) δ ppm 1.31-2.16 (m, 10 H) 2.73-2.89 (m, 1 H) 3.97 (s, 3 H) 4.46 (s, 1 H) 5.00-5.17 (m, 1 H) 7.41-7.47 (m, 1 H) 7.49-7.53 (m, 1 H) 7.55 (s, 1H) 7.57-7.61 (m, 1 H) 7.79 (d, J=8.55 Hz, 1 H) 7.91 (d, J=8.55 Hz, 1 H) 8.18 (s, 1H).

Provenance & Evidence