Sulfuric Acid → HCID 71209104, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (3.05 g, 6.29 mmol) in DCM (85 mL) at 0° C. was added zinc iodide (4.02 g, 12.58 mmol) followed by TMSCN (3.37 mL, 25.2 mmol) and the mixture was stirred at 0° C. for 5 min and then at RT for 30 min. The mixture was diluted with DCM and washed with cold water, dried (Na2SO4) and concentrated. The residue was cooled to 0° C. and MeOH (85 mL) was added followed by dropwise addition of sulfuric acid (16.09 mL, 302 mmol). The mixture was stirred at 80° C. for 26 h, cooled to 0° C. and saturated NaHCO3/water was added slowly followed by solid NaHCO3. The mixture extracted with EtOAc and washed with water, brine, dried (Na2 SO4), concentrated, dried in vacuo to provide methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (3.68 g, 6.23 mmol, 99% yield) as a thick yellowish oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.70 (s, 3 H), 3.47 (br s, 1 H), 3.81 (s, 3 H), 5.42-5.59 (m, 2H), 5.91 (s, 1 H), 6.41 (d, J=3.52 Hz, 1H), 6.93-7.22 (m, 3 H); LCMS (m/z) ES+=473 (M+1).

Provenance & Evidence