Methyl iodide → HCID 66669058, compound

HRID 1617617Notes

Reaction equation

HRID 1617617 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].IC.[CH3:27]N(C)C(=O)C>C1COCC1>[CH3:27][CH:8]([CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 66668653HCID 66668653, compound

Product 1

HCID 66669058HCID 66669058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-diphenyl-1-pyridin-4-yl-propan-1-one (200 mg, example 14, step 1) in THF (11 ml) was added NaH (33 mg as a 55% suspension in mineral oil) at room temperature. The mixture was stirred for 1.5 h and placed in an ice bath. Iodomethane (109 mg) was added. The mixture was stirred for 1 h at 0° C. and for 2 h at room temperature. N,N-dimethylacetamide (0.5 ml) was added and the mixture was stirred overnight at room temperature. Ice water was added and the mixture was extracted with ethyl acetate. The organic phase was dried using MgSO4, filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give the title compound (148 mg) as an off-white solid, MS (ESI+): m/z=302.3 [M+H]+.

Workup

  1. customplaced in an ice bath
  2. stirringThe mixture was stirred for 1 h at 0° C. and for 2 h at room temperature
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1)

Sources & evidence

ORD record
ord-4306807bcfe242208f3bb0b3d47fbfb2
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…