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4-bromo-1-iodo-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulene[ No CAS ]
4-bromo-1-(4-(difluoromethoxy)phenyl)-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
31%
With potassium acetate; sodium carbonate;
Step 3: 4-Bromo-1-(4-(difluoromethoxy)phenyl)-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulene A mixture of 4-bromo-1-iodo-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulene (500 mg, 1.3 mmol), 4-(difluoromethoxy)phenylboronic acid (250 mg, 1.33 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium(II) chloride (100 mg, 0.13 mmol), potassium acetate (2 M solution in water, 2.50 mL, 5.00 mmol) and sodium carbonate (2 M solution in water, 2.5 mL, 5.00 mmol) in acetonitrile (10 mL) was heated under microwave irradiation at 80° C. for 20 min. The reaction mixture was diluted with water and extracted with DCM. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was purified via flash chromatography on silica gel (solvent gradient: 0-10percent methanol in DCM) to yield 160 mg (31percent) of the title compound as an off-white solid. LCMS (ESI): [M+H]+=395/397.
Chemistry
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