Water → HCID 57656392, compound

HRID 911557Notes

Reaction equation

HRID 911557 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[S:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22].C(O[C:29]([F:32])([F:31])[F:30])(=O)C.[Na].[OH2:34]>CN1C(=O)CCC1.CCOC(C)=O.[Cu]I>[C:4]([O:34][C:11]([N:8]1[CH2:9][CH2:10][C:4]2[C:3]([S:19][C:20](=[O:24])[N:21]([CH3:22])[CH3:23])=[C:2]([C:29]([F:30])([F:31])[F:32])[CH:18]=[CH:17][C:5]=2[CH2:6][CH2:7]1)=[O:16])([CH3:10])([CH3:5])[CH3:3]

Participants

7

Reactant 3

HCID 962WaterHCID 57655903HCID 57655903, compoundHCID 86761413HCID 86761413, compound

Product 1

HCID 57656392HCID 57656392, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a stirred solution of 7-bromo-6-dimethylcarbamoylthio-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.383 g, 3.254 mmol), in NMP (40 ml) add sodium trifluoromethyl acetate (3.54 g, 26.03 mmol), copper(I) iodide (2.47 g, 13.0 mmol) and heat the mixture at 180° C. for 4 h. Cool to ambient temperature. Dilute with EtOAc, water and remove the copper solid residue by filtration. Separate the layers of filtrate and extract the aqueous layer three times with EtOAc. Dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (6:1) to give the desired intermediate as a yellow oil (882 mg, 74%).

Workup

  1. temperatureCool to ambient temperature
  2. customremove the copper solid residue
  3. filtrationby filtration
  4. customSeparate the layers of filtrate
  5. extractionextract the aqueous layer three times with EtOAc
  6. dry with materialDry over anhydrous Na2SO4
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (6:1)

Sources & evidence

ORD record
ord-26657f34978d47fd9342c77094ba23b6
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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