Dichloromethane → HCID 86671051, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial were added 2-methyl-propane-2-sulfinic acid [1-(5-bromo-pyridin-2-yl)-cyclobutyl]-amide (33 mg, 0.10 mmol), bis(pinacolato)diboron (30.5 mg, 0.12 mmol, [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with DCM (2.5 mg, 0.003 mmol), potassium acetate (29.4 mg, 0.30 mmol) and DME (1 mL). The reaction mixture was purged using nitrogen and heated in a microwave reactor at 100° C. for 2 h. The reaction mixture was allowed to cool to RT and 7-iodo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione (53.5 mg, 0.10 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dischloropalladium(II), complex with dichloromethane (2.5 mg, 0.003 mmol), sodium carbonate solution (2 M in water, 0.2 mL, 0.4 mmol) and DME (0.5 mL) were added. The reaction mixture was purged using nitrogen and heated in a microwave reactor at 125° C. for 1 h. The reaction mixture was allowed to cool to RT, partitioned between EtOAc and water, and was filtered through a Celite® pad. The aqueous phase was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% MeOH in EtOAc) to afford the title compound (54 mg, 82%). LCMS (Method B): RT=4.90 min, [M+H]+=660.

Provenance & Evidence