1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761875, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(2-bromophenyl)pyrimidine (251 mg, 1.07 mmol), INTERMEDIate M (300 mg, 7.17 mmol), Pd2(dba)3 (65 mg, 0.0717 mmol), Xantphos (82 mg, 0.143 mmol) and sodium-tert-butoxide (137 mg, 1.43 mmol) in toluene (8 mL) was degassed for 10 min. The reaction mixture was subjected to microwave heating for 1 h at 100° C. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 35% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as yellow solid (250 mg, 41.0%); MS (ESI, positive ion) m/z: 572.0 (M+1).

Provenance & Evidence