Potassium Carbonate → HCID 86706951, compound

Participants

Reaction Steps

To a stirred mixture of 4-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C1) (8.2 g, 20 mmol), (3-cyanophenyl)boronic acid (3.2 g, 22 mmol) and potassium carbonate (8.3 g, 60 mmol) in a mixture of 1,2-dimethoxyethane and water (4:1 ratio, 250 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (731 mg, 1.00 mmol). The reaction mixture was degassed and then charged with nitrogen; this procedure was carried out a total of three times. The reaction mixture was heated at reflux for 3 hours, then cooled to room temperature and diluted with saturated aqueous sodium chloride solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel column chromatography (Eluent: 10:1 petroleum ether/ethyl acetate) provided the product as a yellow oil. Yield: 5.0 g, 12 mmol, 60%. 1H NMR (400 MHz, DMSO-d6) δ 8.75 (s, 1H), 8.13 (s, 1H), 8.00-8.02 (m, 1H), 7.84-7.92 (m, 2H), 7.68 (dd, J=7.8, 7.8 Hz, 1H), 5.70 (s, 2H), 3.60 (dd, J=8.0, 8.0 Hz, 2H), 0.86 (dd, J=8.0, 8.0 Hz, 2H), −0.08 (s, 9H).

Provenance & Evidence