Dichloromethane ethanol → HCID 67196582, compound

HRID 1618105Notes

Reaction equation

HRID 1618105 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:25])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH:8]2[CH3:11])=[C:4](I)[CH:3]=1.[Cu][C:28]#[N:29].ClCCl.C(O)C>CN(C)C=O>[C:28]([C:4]1[CH:3]=[C:2]([F:1])[CH:10]=[C:9]2[C:5]=1[C:6](=[O:25])[N:7]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)[CH:8]2[CH3:11])#[N:29]

Participants

5

Reactant 3

HCID 21584144Dichloromethane ethanolHCID 67194682HCID 67194682, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67196582HCID 67196582, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl 4-(6-fluoro-4-iodo-1-methyl-3-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-1-carboxylate (240 mg, 0.5 mmol) and copper(I) cyanide (67 mg, 0.75 mmol) were dissolved in N,N-dimethylformamide (2 mL) and the resulting solution was refluxed under nitrogen atmosphere for 3 hours. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane and washed with 15% ammonium hydroxide. Organic phase was dried over sodium sulfate, filtered and evaporated. Column chromatography (dichloromethane/ethanol:95/5) afforded title compound (174 mg, 93% yield).

Workup

  1. temperaturethe resulting solution was refluxed under nitrogen atmosphere for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with 15% ammonium hydroxide
  5. dry with materialOrganic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7956ac75b01c42bd8c6628196d21a801
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

Loading…