tert-Butyl acetate → HCID 71209175, compound

Participants

Reaction Steps

To a solution of (S)-methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (660 mg, 1.328 mmol) in tert-butyl acetate (15 mL, 111 mmol) was added dropwise in ˜5 min perchloric acid (0.456 mL, 5.31 mmol) (70% reagent) and the mixture was stirred at RT for 1 h. The mixture was carefully quenched with saturated NaHCO3/water and extracted with EtOAc. The organic phase dried (Na2SO4), concentrated, and purified by column chromatography to provide (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (551 mg, 1.032 mmol, 78% yield) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (s, 9 H), 2.74 (s, 3 H), 3.70 (s, 3 H), 5.40 (d, J=2.15 Hz, 2 H), 5.76 (s, 1 H), 6.36 (d, J=3.51 Hz, 1 H), 6.92-7.17 (m, 4 H); LCMS (m/z) ES+=529 (M+1).

Provenance & Evidence