1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761830, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A microwave vial was charged with N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M, 0.320 g, 0.766 mmol), Xantphos (0.089 g, 0.153 mmol), 5-bromo-2-iodobenzonitrile (Combi-Blocks) (0.354 g, 1.150 mmol), Pd2(dba)3 (0.070 g, 0.077 mmol) and sodium tert-butoxide (0.147 g, 1.533 mmol). The mixture was diluted with toluene (7.66 ml), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes, until clean conversion to the desired product. The reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo and the crude material was directly adsorbed onto a 12-g RediSep Gold column and purified by silica gel chromatography, eluting with a gradient of 0% to 100% ethyl acetate in heptane, to provide 4-(4-bromo-2-cyanophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.248 g, 0.415 mmol, 54.2% yield) as yellow solid.

Herkunft & Nachweise