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

HRID 1468176Notes

Reaction equation

HRID 1468176 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

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 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.

Workup

  1. customFlush the vessel with inert gas
  2. customseal
  3. dissolutionDissolve the contents of the vial in 10 mL of a 4:1 dioxane-water mixture and microwave at 150° C. for 5 minutes
  4. additionDilute the reaction mixture with EtOAc
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give an oil
  9. customPurify the residue by flash chromatography

Sources & evidence

ORD record
ord-47a00b2feb4845f982e521bbacb817ad
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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