Potassium Carbonate → 3-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH:15]=[C:14](Br)[CH:13]=[N:12]2)[CH:5]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)#[N:19].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH:15]=[C:14]([C:23]3[CH:24]=[CH:25][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[CH:13]=[N:12]2)[CH:5]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 27343264-Cyanophenylboronic acid

HCID 17024610methyl 3-[(4-bromo-1H-pyrazol-1-yl)methyl]benzoate

Product 1

HCID 675085333-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl esterYield 32%

Procedure

Charge a microwave vial with 3-(4-bromo-pyrazol-1-ylmethyl)-benzoic acid methyl ester (0.60 g, 2.00 mmol), 4-cyanophenylboronic acid (0.35 g, 2.40 mmol), potassium carbonate (0.50 g, 4.80 mmol) and tetrakistriphenylphosphine palladium (0) (0.23 g, 0.2 mmol). Flush the vessel with inert gas and seal. Dissolve the contents of the vial in 10 mL of a 4:1 dioxane-water mixture and microwave at 150° C. for 5 minutes. Dilute the reaction mixture with EtOAc, dry over sodium sulfate, filter and concentrate to give an oil. Purify the residue by flash chromatography using a gradient of 0-50% EtOAc/hexanes to afford 0.20 g, 32% yield of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester as a solid.