Hydrochloric Acid → HCID 89500787, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(tert-butoxycarbonyl)-2-chloro-4H-thieno[3,2-b]pyrrol-5-ylboronic acid (200 mg, 0.66 mmol), N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (160 mg, 0.61 mmol, provided by Chemzon Scientific Inc, Montreal, Canada), Pd(dppf)2Cl2CH2Cl2 (18 mg) and K3PO4 (260 mg) in a 20 mL sealed-tube flask was vented 4 times with nitrogen. 1,4-Dioxane (3 mL and water (0.4 mL) were introduced by syringes and the mixture was vented twice with nitrogen. The reaction mixture was heated at 80° C. for 1 h and TLC showed no starting materials were left. After being cooled to r.t., the reaction mixture was treated with 3 mL of 1N HCl, and stirred for 3 h. The mixture was then extracted with 20 mL of EtOAc, and the extract was dried over Na2SO4, filtered through a pad of silica gel. The filtrate was concentrated under vacuum and the residue was purified by Combiflash on a silica gel column eluted with a gradient of up to 60% EtOAc/hexanes to give 11 mg of the title compound as a solid.

Provenance & Evidence