[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[S:7][CH:6]=1)=[O:4].O.C(OC([N:27]1[C:31]([CH3:32])=[CH:30][C:29](I)=[N:28]1)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:29]2[CH:30]=[C:31]([CH3:32])[NH:27][N:28]=2)[S:7][CH:6]=1)=[O:4]5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-3-carboxylic acid methyl ester (0.10 g, 0.37 mmol) was dissolved in DME (3 mL), IMS 1 mL) and water (0.5 mL) and 3-iodo-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.125 g, 0.41 mmol) was added followed by caesium carbonate (0.18 g, 0.56 mmol). The mixture was degassed and purged with nitrogen then palladium tetrakis(triphenylphosphine) (0.043 g, 0.04 mmol) was added. The reaction mixture was purged with nitrogen then heated by microwave irradiation to 140° C. for 20 minutes. The mixture was diluted with water then extracted with DCM (×3) then the organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on a 5 g silica II cartridge, eluting with 10-33% ethyl acetate in cyclohexane to give the title compound as a tan semi-solid material (0.052 g). LCMS m/z 223.02 [M+H]+ R.T.=2.93 min (Analytical Method 6).
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