Hydrochloric Acid → HCID 71209351, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-(3,4-difluorobenzyl)-4-hydroxy-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5.0 g, 13.7 mmol) in acetonitrile (100 mL) was added pyridine (1.3 mL, 15.77 mmol) and the mixture was cooled to 0° C. and triflic anhydride (2.55 mL, 15.09 mmol) was added dropwise in ˜10 min. The mixture was stirred at RT for 1 h then charged with sodium iodide (10.28 g, 68.6 mmol) in one portion followed by dropwise addition of hydrochloric acid (7.54 mL, 15.09 mmol) (2 M/water). The mixture was stirred at 60° C. for 2 h. Saturated NaHCO3/water was carefully added and the mixture was concentrated and then partitioned between EtOAc and water. The organic phase was washed with satd. Na2S2O3/water, saturated NaHCO3/water, brine, dried (Na2SO4), concentrated to provide ethyl 1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (6.5 g, 12.68 mmol, 92% yield) as a dark oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (t, J=7 Hz, 3 H), 2.65 (s, 3 H), 4.48 (q, J=7 Hz, 2 H), 5.39 (s, 2 H), 6.39 (d, J=3.71 Hz, 1 H), 6.86-7.14 (m, 3 H), 7.17 (d, J=3.71 Hz, 1 H); LCMS (m/z) ES+=457 (M+1).

Provenance & Evidence