Ammonium Chloride → HCID 21106569, compound

Participants

Reaction Conditions

Reaction Steps

1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and DCM (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid. δH (400 MHz, DMSO), 8.28 (1H, s), 7.96 (1H, d), 7.88 (1 H, d), 5.64 (1H, t), 5.31-5.18 (1H, m), 4.78 (2H, d), 1.35 (6H, d) Tr=1.31 min, m/z (ES+) (M+H)+ 297 & 299

Provenance & Evidence