Potassium Carbonate → HCID 89761707, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 4-(2-bromo-4-nitrophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.136 g, 0.220 mmol) (STEP 1, EXAMPLE 64), 3,6-dihydro-2h-pyridine-1-N-boc-4-boronic acid pinacol ester (0.136 g, 0.440 mmol), tetrakis(triphenylphosphine)palladium(0) (0.025 g, 0.022 mmol), and K2CO3 (0.152 g, 1.101 mmol). The solids were diluted with dioxane (1.468 mL) and water (0.734 mL), and the reaction was heated under microwave irradiation at 100° C. for 30 minutes. The reaction was diluted with water and DCM, the layers separated. The aqueous was washed once more with DCM, and the organics were combined and dried using a phase separator to yield material. After concentration under a vacuum, the material was taken up in methanol (and a small amount of DCM) and purified via 5 g SCX column to provide tert-butyl 4-(2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-5-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate, which was taken forward without further purification. m/z (ESI) 720.0 (M+H)+.

Provenance & Evidence