1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761414, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 2-bromo-1-iodo-4-isopropylbenzene (Oakwood, 0.117 g, 0.359 mmol), N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIATE M, 0.150 g, 0.359 mmol), Xantphos (0.042 g, 0.072 mmol), Pd2(dba)3 (0.033 g, 0.036 mmol) and sodium tert-butoxide (0.069 g, 0.719 mmol). The mixture was diluted with toluene (3.59 ml), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes, until clean conversion to the desired product. After completion, the reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo. The crude material was purified using a 5-g SCX column (product eluted with methanol wash to yield 4-(2-bromo-4-isopropylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.175 g, 0.285 mmol, 79% yield) as an orange oil. m/z (ESI) 614.0 (M+H)+.

Provenance & Evidence