To a mixture of 4-[5-bromo-4-(1H-indazol-5-ylamino)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (8 mg, 0.015 mmol), DPPF (4.1 mg, 0.007 mmol), water (0.03 mL) and zinc cyanide (3.7 mg, 0.031 mmol) in acetonitrile (3 mL) was added Pd2 dba3 (3.6 mg, 0.004 mmol) and the mixture was heated to reflux under N2 overnight. The reaction mixture was evaporated and the crude product was purified by preparative TLC using 10% methanol in DCM as eluent to afford 4-[5-cyano-4-(1H-indazol-5-ylamino)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as light gray solid. 1H NMR (400 MHz, CD3OD): δ=8.05 (s, 1H), 7.96 (s, 1H), 7.62 (dd, J=1.8, 0.5 Hz, 1H), 7.50 (s, 1H), 7.27 (dd, J=8.8, 1.9 Hz, 1H), 6.05 (bs, 1H), 5.35 (bs, 1H), 3.93-3.97 (m, 2H), 3.40 (t, J=6.2 Hz, 2H), 2.02-2.07 (m, 2H), 1.37 (s, 9H); MS (ES+): m/z 455.99 (100) [MH+]; HPLC: tR=2.97 min (ZQ2000, polar—5 min).
