Hydrochloric Acid → HCID 11699638, compound

HRID 1173426Notes

Reaction equation

HRID 1173426 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]([CH2:27][C:28]([F:31])([F:30])[F:29])[C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[CH:7][CH:6]=1)=[O:4].[F:34][C:35]([Si](C)(C)C)([F:37])[F:36].[F-].[Cs+].Cl>COCCOC.O>[F:31][C:28]([F:30])([F:29])[CH2:27][N:14]([CH2:13][CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:4])([C:35]([F:37])([F:36])[F:34])[C:2]([F:32])([F:33])[F:1])=[CH:10][CH:9]=1)[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilane2×HCID 11503996HCID 11503996, compound

Product 1

HCID 11699638HCID 11699638, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-[(2-{[4-(trifluoroacetyl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.106 g, 0.22 mmol, example 37) and (trifluoromethyl)trimethylsilane (0.040 mL, 0.26 mmol) in dry DME at rt, under N2, was added anhydrous CsF (0.0020 g, 0.011 mmol). The mixture was stirred 3 h at rt and an additional portion of (trifluoromethyl)trimethylsilane (0.040 mL, 0.26 mmol) was added, and the mixture stirred another 2 h. 2N HCl (5 mL) was added, and the mixture was stirred for 60 h at rt. The mixture was diluted with water and the whole extracted with EtOAc (×2). Combined organics were washed (water, brine, dried over Na2SO4 and concentrated in vacuo, affording 0.051 g of the title compound as a pale yellow solid: MS (ESI) m/z 553 (M−1).

Workup

  1. stirringthe mixture stirred another 2 h
  2. stirringthe mixture was stirred for 60 h at rt
  3. extractionthe whole extracted with EtOAc (×2)
  4. washCombined organics were washed (water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6774280ca834b15b0879bc6e185a356
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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