Lithium Hydroxide → HCID 178480012, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added methyl 1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylate (0.42 g, 0.82 mmol, prepared using D from Preparation #1 with methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-5-carboxylate [Preparation #19]) and NaOH (0.30 g, 7.5 mmol) in 1,4-dioxane (10 mL) and water (2 mL). The mixture was heated to about 85° C. After about 1 h, LiOH (0.196 g, 8.18 mmol) was added and heating was continued at about 100° C. for about 5 h. The mixture was cooled and concentrated under reduced pressure to remove most of the organics. The mixture was diluted with water (30 mL) then adjusted to about pH 4 with AcOH. The mixture was filtered and the solids washed with water (5 mL). The solids were dried to a constant weight under vacuum at about 60° C. to give 1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylic acid the title compound (0.17 g, 60%): LC/MS (Table 2, Method a) Rt=1.73 min; MS m/z 346 (M+H)+. Syk IC50=A.

Provenance & Evidence