Ethyl trifluoroacetate → HCID 117942077, compound

HRID 1499107Notes

Reaction equation

HRID 1499107 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C([O:19][C:20](=O)[C:21]([F:24])([F:23])[F:22])C>C1COCC1>[F:22][C:21]([F:24])([F:23])[C:20]([C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 158289794-bromo-2-methyl-1H-1,3-benzodiazoleHCID 178418339Butyllithium

Product 1

HCID 117942077HCID 117942077, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromo-2-methyl-1H-benzimidazole (500 mg, 2.37 mmol) was dissolved in THF (8 mL) and cooled to −78° C. n-Butyllithium (2.3 mL, 2.5 M in hexanes, 5.7 mmol) was added dropwise and the reaction was stirred at −78° C. for 30 min. Trifluoroacetic acid ethyl ester (339 μL, 2.8 mmol) was added and the reaction was stirred at 0° C. for 1 h. The reaction was quenched with HCl (2 N, 4 mL), then extracted with water and EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (CH2Cl2/MeOH/NH4OH) provided 2,2,2-trifluoro-1-(2-methyl-1H-benzoimidazol-4-yl)-ethanone.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction was stirred at 0° C. for 1 h
  3. customThe reaction was quenched with HCl (2 N, 4 mL)
  4. extractionextracted with water and EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by normal phase silica gel column chromatography (CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-256a140ccdec41728bb3dabaf625b3cc
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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