Potassium Carbonate → Methyl 5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoate

HRID 60889Notes

Reaction equation

HRID 60889 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][N:14]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[N:15]1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1.O>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([C:17]2[CH:16]=[N:15][N:14]([CH3:13])[CH:18]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 15110996Methyl 2-bromo-5-methylbenzoate

Product 1

HCID 117727848Methyl 5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-bromo-5-methylbenzoate (1.01 g, 4.41 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.1 g, 5.28 mmol), Pd(PPh3)4 (0.764 g, 0.66 mmol), K2CO3 (1.83 g, 13.23 mmol) and dioxane/H2O (4:1, 15 mL) was degassed for 10 min and then heated overnight at 100° C. The mixture was cooled, diluted with brine, and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude material, which was purified by silica gel chromatography to obtain the title compound. ESI-MS (m/z): 231 [M+1]+.

Workup

  1. customwas degassed for 10 min
  2. temperatureThe mixture was cooled
  3. additiondiluted with brine
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with saturated NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customto obtain the crude material, which
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b6f08bf4061146c8913a93badd2839dd
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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