Hydrochloric Acid → HCID 68468693, compound

Participants

Reaction Steps

A mixture of 4-(2-bromo-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl)benzoic acid methyl ester (16, R5=CH3, Z=H, 1.9 mmol), butyl vinyl ether (4.8 mmol), Pd(OAc)2 (0.058 mmol), DPPP (0.11 mmol), K2CO3 (2.3 mmol), and H2O (0.3 mL) in DMF (5 mL) is stirred at 120° C. for 1.5 h under nitrogen atmosphere. After cooling to room temperature, the mixture is poured into 1N HCl and extracted twice with EtOAc. The combined extracts are washed with H2O, brine, dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (SiO2; hexane: EtOAc=9:1 to 3:1) to give the ester (19) (R4=CH3, Z=H, R5=CH3) as yellow solid.

Provenance & Evidence