Dimethyl oxalate → HCID 67338224, compound

Participants

Reaction Conditions

Reaction Steps

Tert-BuLi (1.7 M pentane, 27.2 mL, 46.3 mmol) is added to dry THF (195 mL) at −78° C., after few minutes, a solution of 5-bromo-isoquinoline (6.42 g, 30.86 mmol) in THF (5 mL) is added via syringe dropwise. The resulting solution is allowed to stir at −78° C. for 45 minutes, then dimethyl oxalate (11 g, 93 mmol) is added in one portion. After 30 min at −78° C., the reaction is quenched using saturated ammonium chloride solution, diluted with 200 mL EtOAc, and then the TB is removed by rotovap. The residue is diluted with saturated ammonium chloride solution extracted with EtOAc (2×200 mL). The organic layers are combined and washed with 1×75 mL water and 1×75 mL brine, dried over anhydrous sodium sulfate, then concentrated. The material is then purified using flash column chromatography, 20% EtOAC/Hexanes, to yield 3.91 g, 59% of isoquinolin-5-yloxoacetic acid methyl ester. MS (ES, m/z): (M+30 1) 216.1

Provenance & Evidence