Potassium Carbonate → HCID 44193639, compound

Participants

Reaction Steps

6-Bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (61 mg, 0.24 mmol, Bioorg. Med. Chem., 15 (2007), 5912) and bispinacolato diboron (73 mg, 0.29 mmol) were dissolved in 2.5 ml 1,4-dioxane. The solution and flask were purged with argon. Potassium acetate (59 mg, 0.6 mmol) and palladium bis(diphenylphosphino)ferrocene dichloride (10 mg, 0.012 mmol) were added and the sealed reaction was stirred at 100 C. for 3 hr. The reaction was cooled to room temperature and 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (0.1 g, 0.35 mmol) was added. The reaction was diluted with 1 ml 1,4-dioxane and 0.6 ml water. Palladium bis(diphenylphosphino)ferrocene dichloride (15 mg, 0.019 mmol) and potassium carbonate (98 mg, 0.71 mmol) were added. The sealed vial was placed in a microwave reactor and run at 15° C. for 30 min. More palladium catalyst (7 mg, 0.0095 mmol) was added and the reaction repeated at 14° C. for 30 min. The reaction mixture was poured into ethyl acetate and sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined ethyl acetate layers were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to give 31 mg (35%) of the product. MP=>300 C., (M+H)+=379.

Provenance & Evidence