1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-(2-bromo-4-chlorophenyl)-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 (0.500 g, 1.198 mmol), xantphos (0.139 g, 0.240 mmol), 2-bromo-4-chloro-1-iodobenzene (0.570 g, 1.796 mmol), Pd2(dba)3 (0.110 g, 0.120 mmol) and sodium tert-butoxide (0.230 g, 2.395 mmol). The mixture was diluted with toluene (11.98 mL), and purged with nitrogen, and stirred at 130° C. in the microwave for 15 minutes. After completion, 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-chlorophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.576 g, 0.949 mmol) as a light yellow solid.

Provenance & Evidence