Cesium carbonate → 6-(1H-indazol-4-yl)-1-methyl-N-(4-(methylsulfonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (0.04 g, 0.14 mmol) in dioxane was treated with 4-methylsulphonylaniline hydrochloride (0.058 g, 0.28 mmol) in the presence of (tris(dibenzylidene acetone)dipalladium(0), Pd2(dba)3 (0.13 g, 0.014 mmol), XANPHOS (0.016 g, 0.028 mmol) and cesium carbonate (0.18 g, 0.56 mmol) and the reaction mixture were heated overnight at 100° C. The reaction mixture was diluted with ethylacetate and water. The aqueous portions were extracted with ethyl acetate and the organic portions pooled and dried over anhydrous sodium sulfate. The solvent were removed and the crude material purified (Biotage) to obtain 10 mg of 104. 1H NMR (400 MHz, MeOD) δ 8.69 (s, 1H), 8.12 (s, 1H), 7.97 (d, J=8.7, 2H), 7.78-7.55 (m, 4H), 7.59-7.44 (m, 2H), 4.17 (s, 3H), 3.35 (s, 1H), 3.14 (s, 3H). MS (ESI) m/z 419.2 (M+1)+

Provenance & Evidence