Dichloromethane → HCID 178434533, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (200 mg, 0.51 mmol), 3-methylpyrazole-4-boronic acid pinacol ester (117 mg, 0.56 mmol), PdCl2dppf.DCM (42 mg, 0.05 mmol) and Cs2CO3 (416 mg, 1.28 mmol) in dioxane (4 mL) and H2O (1 mL) was purged with argon and heated at 80° C. for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-3% MeOH in DCM) affording 9-Bromo-2-(3-methyl-1H-pyrazol-4-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (53 mg, 30%). LCMS: RT 2.21 min [M+H]+ 345.3

Provenance & Evidence