Sodium Hydroxide → 2-(5-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl2-(1-methyl-5-(methylsulfonyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (80 mg, 0.16 mmol) in dioxane/water (6 mL/4 mL) was added NaOH (100 mg, 2.5 mmol), the reaction mixture was heated to 85° C. with stirring for 4 hours, the dioxane was removed under reduced pressure, the aqueous layer was adjusted to pH=4 with 2 N HCl. The formed precipitate was collected by filtration, washed with water (3 mL) and dried to afford 2-(5-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (40 mg, 67.7%) as an orange solid. LCMS: (M+H)+=372; 1H NMR (300 MHz, DMSO): δ 12.89 (d, 1H, J=2.7 Hz), 12.49 (brs, 1H), 9.47 (s, 1H), 9.08 (s, 1H), 8.50 (d, 2H, J=3.3 Hz), 8.01-7.95 (m, 1H), 4.23 (s, 3H), 3.27 (s, 3H).

Provenance & Evidence