A mixture of tert-butyl (1S,2R)-2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (200 mg, 0.364 mmol), sodium carbonate (77 mg, 0.729 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (91 mg, 0.437 mmol) and bis(triphenylphosphine)palladium chloride (25.6 mg, 0.036 mmol) in DME (2 mL) and H2O (0.667 mL) was stirred at 85° C. for 2 h. To the resulting mixture was added EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2(Hexane/EtOAc=2/3) to give the title compound as a yellow oil (88 mg, 40.6%). 1H NMR (500 MHz, CDCl3) δ ppm 1.28-2.01 (m, 17 H), 3.80 (d, J=2.93 Hz, 3 H), 3.85 (s, 3 H), 3.91-4.01 (m, 4 H), 4.23 (br s, 2 H), 4.41 (br s, 1 H), 4.68 (d, J=1.95 Hz, 2 H), 5.36 (br s, 1 H), 6.36-6.54 (m, 2 H), 7.15-7.21 (m, 1 H), 8.26 (br s, 1 H), 9.02 (br s, 1 H). [M+H] calc'd for C31H39FN6O5, 595; found, 595.
