Methanol → HCID 68328196, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.750 g, 1.696 mmol) in DCM (8.5 mL) and a few drops of DMF was added oxalyl chloride (0.259 mL, 2.97 mmol) at RT. After 30 min, the reaction was cooled to 0° C., MeOH was added and the mixture was stirred for 30 min. The mixture was then concentrated. To the yellow solid was added H2O and the mixture was extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give methyl 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.700 g, 1.534 mmol, 90%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 457.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 2.38 (3H, s), 4.01 (3H, s), 7.27-7.32 (2H, m), 7.75-7.81 (2H, m), 8.02 (1H, s), 8.18 (1H, d, J=8.80 Hz), 8.34 (1H, d, J=8.61 Hz).

Provenance & Evidence