Ethyl trifluoroacetate → HCID 59240304, compound

HRID 1673035Notes

Reaction equation

HRID 1673035 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[C:4]([Cl:23])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:34][C:35]([F:42])([F:41])[C:36](OCC)=[O:37]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH2:14][C:36](=[O:37])[C:35]([F:42])([F:41])[F:34])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[C:4]([Cl:23])[CH:3]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 2733832Lithium HexamethyldisilazideHCID 59240515HCID 59240515, compound

Product 1

HCID 59240304HCID 59240304, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a dry N2 purged 50 mL round bottom flask attached with addition funnel was added 1-(1-(4-bromo-2-chlorophenyl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)ethanone (640 mg, 1.56 mmol) and anhydrous THF (12 mL). The reaction solution was cooled to −78° C. prior to dropwise addition of a 1.0 M LHMDS solution in THF (1.72 mL). The enolate solution was allowed to stir, warming to −200C over 1 h. The reaction solution was cooled to −600C, and ethyl trifluoroacetate (370 μL, 3.12 mmol) was added. The reaction solution was stirred at room temperature for 16 h. The reaction solution was quenched with H2O and diluted with EtOAc (100 mL). The EtOAc phase was partitioned, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed through a 12 g SiO2 column using a 100% hexane to 60% EtOAc gradient to yield 120 mg (86% yield) of title compound. MS (ESI) 507.0, 509.0 [M+H]+.

Workup

  1. customTo a dry N2 purged 50 mL round bottom flask
  2. additionattached with addition funnel
  3. temperaturewarming to −200C over 1 h
  4. additionwas added
  5. stirringThe reaction solution was stirred at room temperature for 16 h
  6. customThe reaction solution was quenched with H2O
  7. additiondiluted with EtOAc (100 mL)
  8. customThe EtOAc phase was partitioned
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude material was chromatographed through a 12 g SiO2 column

Sources & evidence

ORD record
ord-f19cd84026af4c8686a044cfc4ddb7f3
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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