[CH3:1]OB1C2CCCC1CCC2.C[Li].[CH3:14][O:15][C:16]([C:18]1[C:19]([NH2:29])=[C:20]([Cl:28])[CH:21]=[C:22]2[C:26]=1[NH:25][N:24]=[C:23]2Br)=[O:17]>O1CCCC1.C(OCC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Pd+2]>[CH3:14][O:15][C:16]([C:18]1[C:19]([NH2:29])=[C:20]([Cl:28])[CH:21]=[C:22]2[C:26]=1[NH:25][N:24]=[C:23]2[CH3:1])=[O:17]To a solution of 899 mg (5.91 mmol) of 9-methoxy-9-bora-bicyclo[3.3.1]nonane in 5 mL of anhydrous tetrahydrofuran is added dropwise 3.71 mL (5.91 mmol) of a solution 1N of methyl lithium in diethylether. After few minutes of stirring, a mixture of 6-amino-3-bromo-5-chloro-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 39, and 104 mg (0.15 mmol) of bis(triphenylphosphine) palladiumI(II) dichloride in 10 mL of anhydrous tetrahydrofuran is added. The reaction mixture is stirred in a microwave oven at 150° C. for 15 minutes. After filtration over Celite and concentration in vacuo, the residue is purified by flash chromatography (SiO2, hexanes/ethyl acetate 1:1) to afford 470 mg of product (66%) as a pale yellowish solid; LC/MS:240/242 (M+H)+.
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