4-(Trifluoromethyl)phenylboronic acid → HCID 44818303, compound

HRID 1748604Notes

Reaction equation

HRID 1748604 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[C:7](Br)=[N:8][CH:9]=1)=[O:4].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>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.O1CCCC1.O.C(=O)([O-])[O-].[Na+].[Na+].O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[C:7]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[N:8][CH:9]=1)=[O:4]

Participants

7

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 26343677Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate

Product 1

HCID 44818303HCID 44818303, compoundYield 94.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 2735133Sodium Carbonate MonohydrateSolventHCID 178418397HCID 178418397, compoundSolvent

Conditions

Temperature
120 °C

Procedure

To 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (800 mg) were added 4-(trifluoromethyl)phenylboronic acid (1.04 g), and tetrakis(triphenylphosphine)palladium(0) (422 mg), and tetrahydrofuran (9 ml), saturated sodium carbonate water (3 ml), and water (1.5 ml) as solvents, and stirred at 120° C. for 30 minutes under microwave radiation. After completion of the reaction, to the reaction solution 6 was added water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 3-methyl-2-[4-(trifluoromethyl)phenyl]-3H-imidazole-4-carboxylic acid methyl ester (980 mg) as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b9544f31311b4d0f8ebed1b3d0ac086f
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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