Methanol → HCID 178437817, compound

HRID 1754370Notes

Reaction equation

HRID 1754370 reaction equation
I[C:2]1[NH:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([F:11])([F:10])[F:9].C([O-])([O-])=O.[K+].[K+].CO.CO[CH2:22][CH2:23]OC>O.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>[CH3:7][C:5]1[NH:6][C:2]([CH:22]=[CH2:23])=[C:3]([C:8]([F:11])([F:10])[F:9])[N:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 178432833HCID 178432833, compound

Product 1

HCID 178437817HCID 178437817, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-iodo-2-methyl-4-(trifluoromethyl)-1H-imidazole (1.98 g, 7.2 mmol) in DME (20 mL) and H2O (4 mL) was added K2CO3 (10 g, 71.9 mmol), trivinylboronic anhydride pyridine complex (1.73 g, 7.19 mmol) and Pd(PPh3)4 (830 mg, 0.719 mmol). The resulting reaction mixture was stirred at 80° C. for 3 h. MeOH (100 mL) was then added to the reaction mixture and the mixture was filtered, concentrated in vacuo, and purified by flash chromatography (SiO2, 10% MeOH/CH2Cl2) to obtain 2-methyl-4-(trifluoromethyl)-5-vinyl-1H-imidazole (911 mg, 5.17 mmol, 72% yield) as a brown syrup.

Workup

  1. customThe resulting reaction mixture
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (SiO2, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-36d69de34f3e4b71b6c2cd86e0dba1a4
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

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