Potassium Carbonate → 3-[2-(4-Methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-4-methyl-benzoic acid, methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Methoxycarbonyl-2-methylphenylboronic acid	HCID 12163650	—
Reactant	6-Bromo-2-[(4-methoxyphenyl)methyl]-1(2H)-isoquinolinone	HCID 57551771	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-[2-(4-Methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-4-methyl-benzoic acid, methyl ester	HCID 57551747	—

Reaction Conditions

Temperature	95 °C

Reaction Steps

A mixture of 6-bromo-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (product of step iv)) (1.2 g), intermediate 2 (0.7 g), potassium carbonate (1.0 g) and tetrakis(triphenylphosphine)palladium(0) (0.4 g) in N,N-dimethylformamide (20 mL) was heated to 95° C. for 17 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried, filtered and evaporated. The residue was purified (SiO2, 1:2 ethyl acetate:iso-hexane as eluent) to yield the sub-titled compound (1.03 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08012979B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-1e60c41417c649c7a49624cbeb823323
Source note	uspto-grants-2011_09