Dichloromethane → 2-(1-(4-amino-3-(1H-indazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one

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To a solution of Example 57c (0.500 g, 0.758 mmoles) in DMF (4.5 ml), ethanol (2.3 ml) and water (2.3 ml), Indazole-6-boronic acid pinacol ester (0.462 g, 1.89 mmoles) and sodium carbonate (0.502 g, 4.74 mmoles) were added and the system is degassed for 30 min. Tetrakistriphenylphosphine Palladium (0.215 g, 0.186 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as brown solid (0.080 g, 16% yield). MP: 206-208° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.19(s,1H), 8.14(s,1H), 8.08(s,1H),8.05(dd, J=7.9,1.5 Hz, 1H), 7.90(d, J=8.3 Hz, 1H), 7.86(m,1H), 7.71(s,1H), 7.69(d, J=8.4 Hz, 1H), 7.53(t, J=7.1 Hz, 1H), 7.39(dd, J=8.2,1.1 Hz, 1H), 7.30(m,2H), 7.07(dt, J=8.7,2.6 Hz, 1H), 6.92(br m, 2H), 6.06(q, J=7.1 Hz, 1H), 1.91(d, J=7.0 Hz, 3H). Mass: 517.96(M+).

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