Dimethylformamide → HCID 86640983, compound

Participants

Reaction Steps

A stirred solution of 3-(6-bromo-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl pivalate (51.3 g) in DMF (150 mL) at 75° C. (flask fitted with a CaCl2 drying tube) was treated dropwise over ˜20 min with a freshly prepared solution of Vilsmeyer Haak reagent [freshly prepared by dropwise addition of POCl3 (182 mL) over ˜40 min to DMF (302 mL) at 0° C. and then stirred for 1 h at room temperature]. Heating was continued for 8 h, and then the reaction mixture was cooled to room temperature and stirred overnight. The mixture was poured onto ice water (6 L) [CAUTION: exotherm] and extracted with tert-butyl methyl ether (2×2.5 L). The combined organics were washed with 20% w/v aqueous brine (2.5 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified (SiO2 chromatography, eluting with 10% to 20% ethyl acetate/isohexane) to give the subtitle product (41.5 g).

Provenance & Evidence