Acetic Anhydride → HCID 18797393, compound

HRID 1456998Notes

Reaction equation

HRID 1456998 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=1.[H-].[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C)C=O>[C:20]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5]([C:11]2[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=2)=[CH:6]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 149732095-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Product 1

HCID 18797393HCID 18797393, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.90 gm (3.94 mMol) 5-fluoro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 20 mL dimethylformamide were added 0.17 gm (4.3 mMol) sodium hydride (60% dispersion in mineral oil). The mixture was stirred for one hour at room temperature at which time 0.47 mL (5.0 mMol) acetic anhydride were added. The reaction mixture was then concentrated under reduced pressure and the residue partitioned between chloroform and water. The organic phase was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromaography, eluting with chloroform containing 5% methanol. Fractions containing product were combined and concentrated under reduced pressure to give 0.92 gm (86%) of the title compound as a faintly yellow crystalline solid.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue partitioned between chloroform and water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with chloroform containing 5% methanol
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b5b37b03a51442a852d0a03c2840b88
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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