Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:15]3[CH:16]=[N:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:19]=3)[N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][N:35]=1.O>CC(O)(C)C.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:40][C:37]1[CH:38]=[CH:39][C:34]([NH:33][C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[C:9]([C:15]4[CH:16]=[N:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:19]=4)[N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[C:4]=3[CH:3]=2)=[N:35][CH:36]=1Pd2(dba)3 (9.0 mg, 0.01 mmol) was added to a mixture of tert-butyl 4-(6-chloro-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (15) (39 mg, 0.098 mmol), cesium carbonate (128 mg, 0.393 mmol), 2-amino-5-fluoropyridine (22 mg, 0.197 mmol) and di-tBuX-Phos (16.7 mg, 0.039 mmol) in t-BuOH containing water (3%) (1.1 mL). The reaction mixture was heated at 80° C. for 1.5 hr under microwave irradiation. It was then diluted with EtOAc and washed with water. The organic extracts were dried over MgSO4, filtered and concentrated under vacuum. The residue was then purified by prep TLC (DCM/MeOH, 95/5) to afford 17 mg of title compound mixed with some 2-amino-5-fluoropyridine. This mixture was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) 1.70 (s, 9H), 2.97 (s, 3H), 6.72 (d, J=0.9 Hz), 7.37-7.41 (m, 1H), 7.52-7.56 (m, 1H), 7.62 (br s, 1H), 7.95 (m, 1H), 8.17-8.19 (m, 1H), 8.26 (s, 1H), 8.38 (s, 1H), 8.54 (d, J=0.9 Hz, 1H).
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