Water → HCID 86649119, compound

Participants

Reaction Steps

The product from Example 187A (1.4 g, 2.396 mmol), 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (0.695 g, 2.396 mmol), potassium phosphate (1.017 g, 4.79 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.022 g, 0.024 mmol) and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (0.021 g, 0.072 mmol) were combined in THF (18 mL)/water (6 mL). The mixture was sparged with nitrogen for 15 minutes, stirred for 6 hours diluted into EtOAc, washed with 1M sodium bicarbonate, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on an Isco 120 g silica cartridge eluting with 20-60% EtOAc in hexane gave the title compound as a yellow glass (1.1 g, 74%). MS (ESI) m/z 620 (M+H)+.

Provenance & Evidence