Methyl iodide → HCID 57656571, compound

HRID 911414Notes

Reaction equation

HRID 911414 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:24]=[CH:23][C:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:16][C:10]=2[C:9]=1O.CI>CC(C)=O>[Br:7][C:8]1[CH:24]=[CH:23][C:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:22])[C:18]([F:19])([F:21])[F:20])[CH2:15][CH2:16][C:10]=2[C:9]=1[O:4][CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57655992HCID 57655992, compound

Product 1

HCID 57656571HCID 57656571, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add potassium carbonate (10.214 g, 73.9 mmol) to a solution of 7-bromo-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (5.0 g, 14.8 mmol) in acetone (50 mL) and stir for 10 min. Add methyl iodide (4.2 g, 1.5 mL, 29.6 mmol) and stir the mixture overnight at room temperature. Remove the solvent in vacuo and partition the residue between water and DCM. Extract the aqueous phase twice with DCM. Combine the organic extracts, dry over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate as a solid (5.15 g, 99%). MS (ES+) m/z: 352 (M+H)+.

Workup

  1. customRemove the solvent in vacuo
  2. custompartition the residue between water and DCM
  3. extractionExtract the aqueous phase twice with DCM
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-72fe747b40b24f65bed8725540f30040
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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