Hydrochloric Acid → HCID 68467336, compound

Participants

Reaction Steps

A solution of 4-[5,7,7,10,10-pentamethyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-7,8,9,10-tetrahydro-5H-5,13diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl]benzoic acid methyl ester (17) (R5=CH3, Z=H, 0.89 mmol) and phenyl boronic acid (1.8 mmol) in THF(=tetrahydrofuran)/MeOH (4:3, 14 mL) is treated with 2 N HCl (14 mL). After stirring for 5 h, the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting residue is purified by flash column chromatography (SiO2; hexane: EtOAc 4:1 to 1:1) to give 12-(4-methoxycarbonylphenyl)-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]cyclohepta[1,2-b]naphthalene-2-boronic acid (18) (R4=CH3, Z=H) contaminated with phenyl boronic acid.

Provenance & Evidence