[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]1[CH:12]=[C:11](Br)[CH:10]=[N:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:15]1(B(O)O)[CH2:17][CH2:16]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:15]1([C:11]2[CH:10]=[N:9][N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14])[CH:12]=2)[CH2:17][CH2:16]1Palladium acetate (215 mg, 0.957 mmol) was added to tert-butyl[4-bromo-1H-pyrazol-1-yl]acetate (5 g, 19.14 mmol) (see Preparation 86), cyclopropyl boronic acid (8.22 g, 95.74 mmol), potassium phosphate (8.12 g, 38.29 mmol) and tricyclohexylphosphine (537 mg, 1.91 mmol) in toluene: water (60 mL:15 mL). The mixture was degassed for 20 minutes then refluxed for 18 hours. The reaction mixture was filtered through Celite™, the filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (gradient of EtOAc:hexane 15:85) to afford the title compound as an off white solid in 21% yield, 1.3 g.
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