1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761565, compound

Participants

Reaction Steps

A mixture of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M; 700 mg, 1.674 mmol), 1-(2-bromophenoxy)-2-methylpropan-2-ol (2.8 g, 11.722 mmol), Pd2(dba3)2 (96 mg, 0.1674 mmol), Xantphos (306 mg, 0.3349 mmol) and sodium-tert-butoxide (402 mg, 4.186 mmol) in toluene (15 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected to microwave for 1 h at 100° C. After completion, 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 crude material, which was purified by combiflash silica gel column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane) to yield 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 88.2%). m/z (ESI) 582.1 (M+H)+.

Provenance & Evidence