Sodium Carbonate → HCID 57576711, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing mixture of acetone O-{[4-amino-7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl}oxime (prepared as described in Example 96, 1.16 g, 2.86 mmol), phenylboronic acid (0.42 g, 3.43 mmol), triphenylphosphine (7 mg, 0.026 mmol), 2 M aqueous sodium carbonate (4.3 mL, 8.58 mmol), and 5:1 propanol/water (18 mL) was evacuated under reduced pressure and back-filled with nitrogen gas. Palladium(II) acetate (2 mg, 0.009 mmol) was added, and the flask was again evacuated and back-filled with nitrogen gas. The reaction mixture was heated at 100° C. for 18 hours. The reaction mixture was allowed to cool to room temperature and was diluted with dichloromethane (40 mL) and water (30 mL). The aqueous layer was extracted with dichloromethane (2×15 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a tan solid. The solid was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform) to afford a thick oil that was crystallized from acetonitrile. The crystals were isolated by filtration and dried at 80° C. in a vacuum oven to yield 0.501 g of acetone O-{[4-amino-1-(2-methylpropyl)-7-phenyl-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl}oxime as a white powder, mp 196-197° C.

Provenance & Evidence