1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761916, compound

Participants

Reaction Conditions

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; 500 mg, 1.19 mmol), 1-bromo-2-(methoxymethoxy)benzene (1.2 g, 5.98 mmol), Pd2(dba)3 (109 mg, 0.119 mmol, GLR), Xantphos (138 mg, 0.23 mmol, GLR) and sodium-tert-butoxide (229 mg, 2.39 mmol) in toluene (15 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 100° C. for 1 h under microwave. After completion, the reaction mixture was diluted with water (15 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: 0-20% ethyl acetate in hexane) to yield N-(4-methoxybenzyl)-4-(2-(methoxymethoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 90.7%). MS (ESI, positive ion) m/z; 554.1 (M+1).

Provenance & Evidence