Water → HCID 18385105, compound

HRID 2298246Notes

Reaction equation

HRID 2298246 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 678615-FluoroindoleHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 18385105HCID 18385105, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3 g (22.2 mmol) of 5-fluoroindole in 90 ml of dry DMF was added 8.28 g (23 mmol) NaH and 4.51 g (23 mmol) of 3-bromomethyl benzonitrile. The mixture was stirred overnight at and thereafter distributed between water and dihcloromethane. The water layer was extracted twice with dichloromethane, and the combined organic extracts were washed with brine, dried and evaporated. The oily residue was subjected to flash chromatography eluting with dichloromethane/hexane (1/1), to give 5.75 g (76%) of the subtitle product.

Workup

  1. extractionThe water layer was extracted twice with dichloromethane
  2. washthe combined organic extracts were washed with brine
  3. customdried
  4. customevaporated
  5. washeluting with dichloromethane/hexane (1/1)

Sources & evidence

ORD record
ord-986b54b40865487a90a8b55d1ef43d18
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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