Triethylamine → 3-((4-(6-Bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazol-1-yl)methyl)-5-methylisoxazole

Participants

Reaction Conditions

Reaction Steps

Bis(triphenylphosphine)palladium dichloride (46 mg, 0.066 mmol) was added to a solution of N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide (8) (0.5 g, 1.32 mmol), 3-((4-ethynyl-1H-pyrazol-1-yl)methyl)-5-methylisoxazole (32) (0.278 g, 1.48 mmol), triethylamine (0.7 g, 7 mmol) and copper iodide (13 mg, 0.065 mmol) in DMF (5 ml). The reaction mixture was heated for 1 h at 60° C. The reaction mixture was cooled to room temperature and diluted with water (20 ml) and dichloromethane (30 ml). The organic solution was dried and concentrated in vacuo. The crude product was purified by flash silica chromatography (10 to 20% ethyl acetate in hexane) to afford the product as a white powder (300 mg, 51.8%). 1H-NMR (500 MHz, CDCl3) 2.43 (s, 3H), 2.96 (s, 3H), 5.41 (s, 2H), 6.02 (s, 1H), 6.69 (s, 1H), 7.78 (s, 1H), 7.87 (s, 1H), 8.22 (s, 1H), 8.62 (s, 1H).

Provenance & Evidence