[CH2:1]=[C:2](B(O)O)[CH3:3].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)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.[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH2:1]=[C:2]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2)[CH3:3].[NH:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:16][CH:15]=2)[CH:11]=[N:12]1A mixture of prop-1-en-2-ylboronic acid (1.2 g), 5-bromo-1H-indazole (1.0 g, 5.1 mmol), Pd(dba)2 (0.04 g, 0.07 mmol), X-phos (0.04 g, 0.08 mmol) and Cs2CO3 (3.0 g, 9.2 mmol) in a mixture of 30 mL of DMF and 5 mL of water was stirred at 130° C. under nitrogen for 8 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (200-300 mesh, eluting with a mixture of ethyl acetate and petroleum ether (1:5, v/v) to give a 2:3 mixture 5-(prop-1-en-2-yl)-1H-indazole and 1H-indazole (0.9 g). The crude mixture was used into the next step without further purification. LCMS: (M+H)+=159; 1H NMR (300 MHz, DMSO): δ 8.08 (s, 1H), 7.81-7.80 (m, 1H), 7.62 (dd, 1H, J1=8.7 Hz, J2=1.5 Hz), 7.53-7.46 (m, 1H), 5.40-5.39 (m, 1H), 5.12-5.11 (m, 1H), 2.24 (s, 3H).
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