[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]2[C:6](I)=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:28]B1OB(C)OB(C)O1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]2[C:6]([CH3:28])=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1
A mixture of 6-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (600 mg, 1.550 mmol), K3PO4 (644 mg, 3.037 mmol), PdCl2(dppf) (186 mg, 0.228 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (290 mg, 1.52 mmol) in dioxane (2 mL) under nitrogen in a sealed vial was heated at 100° C. in a microwave oven for 18 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated in vacuo to afford 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (230 mg, 53.9%). MS (ESI): m/z=276 [M+1]+.
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