Dimethylformamide → HCID 21950045, compound

HRID 2215751Notes

Reaction equation

HRID 2215751 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12]N(C)C)=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[C-]#N.[Na+].[CH3:21][N:22](C=O)C>CCOC(C)=O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][C:21]#[N:22])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 13594136HCID 13594136, compound

Product 1

HCID 21950045HCID 21950045, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Trifluoromethyl-N,N-dimethyl-1H-indole-3-methanamine (1.2 g, 4.95 mmol) and NaCN (0.72 g, 14.86 mmol, 3.0 eq.) were combined with DMF (10 mL) and EtOAc (2 mL). The mixture was heated to reflux for 6 hours, then cooled to rt. The product was extracted with EtOAc and the organic layer was washed with water and dried (MgSO4). The solvent was removed in vacuo to give 0.66 g (60%) of the title compound after column chromatography (Hex:EtOAc 1:1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionThe product was extracted with EtOAc
  4. washthe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f3d9c965dcd24de6a06353896afe05d1
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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