Cl[C:2]1[CH:7]=[C:6]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH:27]([F:29])[F:28])=[C:21]([CH3:30])[N:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:4][N:3]=1.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[N:36][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:28][CH:27]([F:29])[O:26][C:22]1[C:23]([CH3:25])=[CH:24][C:19]([C:8]2([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:34]4[CH:35]=[N:36][CH:37]=[C:32]([F:31])[CH:33]=4)[CH:7]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)=[N:20][C:21]=1[CH3:30]A mixture of 3-(2-chloro-pyridin-4-yl)-3-(5-difluoromethoxy-4,6-dimethyl-pyridin-2-yl)-7-fluoro-3H-isoindol-1-ylamine 1 (0.14 g, 0.32 mmol), 5-fluoropyridine-3-boronic acid (0.068 g, 0.485 mmol), Pd(PPh3)4 (0.065 g, 0.056 mmol), aqueous Na2CO3 (2M, 1 mL, 2 mmol) in DME (4 mL) was degassed for 15 minutes using nitrogen and then heated in a sealed tube at 90° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (20 mL) and washed with saturated NaHCO3 solution (10 mL) and H2O (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (22 mg, 14%). 1H NMR (400 MHz, CDCl3) δ ppm 8.92 (br. s., 1 H) 8.61 (d, 1 H) 8.48 (br. s., 1 H) 8.00 (d, 2 H) 7.85 (s, 1 H) 7.54-7.61 (m, 1 H) 7.51 (s, 1 H) 7.40 (d, 1 H) 7.16 (t, 1 H) 6.36 (s, 1 H) 2.51 (s, 3 H) 2.30 (s, 3 H).
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