1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with INTERMEDIATE M (0.573 g, 1.372 mmol), Xantphos (0.159 g, 0.274 mmol), 2-bromo-1-iodo-4-trifluoromethyl-benzene (0.722 g, 2.059 mmol), Pd2(dba)3 (0.126 g, 0.137 mmol) and sodium tert-butoxide (0.264 g, 2.74 mmol). The mixture was diluted with toluene (13.72 mL), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes. The reaction was diluted with water, and washed with DCM. The organics were dried using a phase separator, and concentrated under a vacuum. The material was then purified via silica gel MPLC, eluting with 0 to 50% ethyl acetate in heptanes to yield 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a light yellow solid.

Provenance & Evidence