Hydrochloric Acid → HCID 66793770, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(5-amino-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one, prepared as described in Example 3, (35 mg, 0.146 mmol), in dichloromethane (2.0 mL) was added diisopropylethylamine (75 pt, 0.44 mmol). The reaction was cooled to −10° C. and methanesulfonyl chloride (22 μL, 0.28 mmol) was added. After 15 minutes the reaction was quenched with saturated aqueous sodium bicarbonate and diluted with dichloromethane. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated. The resulting residue was dissolved in methanol (5 mL) and treated with 2 M aqueous sodium hydroxide (0.5 mL, 1 mmol) and permitted to stir at room temperature for 10 minutes. The reaction was then diluted with dichloromethane and water and the pH of the solution was brought to ca. 7 via the careful addition of 1M aqueous HCl. The layers were separated and the aqueous layer was extracted four additional times with dichloromethane and one time with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 7%) to furnish N-[5-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-pyridin-3-yl]-methanesulfonamide; HRMS: (ES+) m/z 318.0912 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 3.11 (s, 3H), 3.28 (s, 3H), 3.62 (s, 2H), 6.94 (d, J=8.1 Hz, 1H), 7.50 (s, 1H), 7.51-7.59 (m, 1H), 7.91 (s, 1H), 8.41 (d, J=2.5 Hz, 1H), 8.67 (d, J=1.8 Hz, 1H).

Provenance & Evidence