1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(4-methoxybenzyl)-4-(2-(tetrahydro-2H-pyran-4-yl)phenyl)-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 N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.120 g, 0.287 μmol), 4-(2-iodophenyl)tetrahydro-2H-pyran (0.124 g, 0.431 μmol), sodium tert-butoxide (0.055 g, 0.575 μmol), tris(dibenzylideneacetone)dipalladium(0) (0.026 g, 0.029 μmol) and xantphos (0.033 g, 0.057 μmol). After purging with N2, toluene (3 mL) was added and the vessel was sealed and heated in the microwave at 130° C. for 30 min. LCMS confirmed coupling product formation. The reaction mixture was concentrated and taken up in DCM, then passed through a 12 g silica gel plug, eluting with 1:1 EtOAC/hex to afford N-(4-methoxybenzyl)-4-(2-(tetrahydro-2H-pyran-4-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a semi-pure orange solid.

Provenance & Evidence