Sodium Cyanide → HCID 22262925, compound

HRID 489718Notes

Reaction equation

HRID 489718 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11]N(C)C)=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:15].[C-:16]#[N:17].[Na+]>C(OCC)(=O)C.CS(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:16]#[N:17])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 22262909HCID 22262909, compound

Product 1

HCID 22262925HCID 22262925, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (6-Bromo-5-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (1.0 g) and sodium cyanide (0.54 g, 11.02 mmol) in ethyl acetate (1.8 ml) and methylsulfoxide (16 ml) was heated at 80° C. for 24 hrs then partitioned between ethyl acetate and water. The organic extract was washed with brine, dried (anhydrous sodium sulfate), concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 20% ethyl acetate in hexane to give (6-Bromo-5-fluoro-1H-indol-3-yl)-acetonitrile as a yellow solid (0.41 g, 44%). 1H NMR (CDCl3) d: 3.78 (d, 2H, J=1.0 Hz), 7.27 (dd, 1H, J=1.2 Hz), 7.31 (d, 1H, J=8.8 Hz, 7.58 (d, 1H, J=5.5 Hz), 8.23 (bs, 1H).

Workup

  1. customthen partitioned between ethyl acetate and water
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography over silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9c53fb2fe15d41cba2dff8f4e4a5deb4
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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