1,4-Dioxane → HCID 89510077, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(tert-butoxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-2-ylboronic acid (150 mg, 0.57 mmol), N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (114 mg, 0.44 mmol, provided by Chemzon Scientific Inc, Montreal, Canada), Pd(dppf)2Cl2CH2Cl2 (16 mg, 0.02 mmol) and K3PO4 (187 mg, 0.88 mmol) in a 20 mL sealed-tube flask was vented 4 times with nitrogen. 1,4-Dioxane (2.2 mL) and water (0.3 mL) were introduced by syringe and the mixture was vented twice with nitrogen. The reaction mixture was then heated at 80° C. for 2 h and TLC showed no starting materials were left. EtOH (15 mL) and water (5 mL) were added and the reaction mixture was stirred for 0.5 h at r.t. and then extracted with 2×15 mL of EtOAc. The extracts were dried over Na2SO4, filtered through a pad of silica gel. The filtrate was concentrated under vacuum to give 15 mg of the title compound as a dark solid.

Provenance & Evidence