8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one → 8-[[2-[(1,3-Dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one

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A suspension of 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (23.06 mg, 0.13 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol) and cesium carbonate (85 mg, 0.26 mmol) was stirred at 80 °C overnight under nitrogen. LCMS showed formation of more bis-arylation by-product than in _EN01775-08_ (DMA under micorwaves conditions). The crude was combined with EN01775-08-01 and poured onto a silicagel column. The crude product was purified by flash chromatography eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness to afford a gummy film in the flask **(37mg: not that bad)**. it was scratched in diethyl ether (soluble) then after Et2O evaporation in a few drops of MeCN. A solid crashed out. The resulting solid was taken up into diethyl ether, collected by filtration and dried to afford 8-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (19.00 mg, 33.7 %) as a white solid (a bit soluble in Et2O because some P1 remained in the Et2O filtrate). **not the real yield**

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