Sodium hydride → HCID 66924281, compound

HRID 1364460Notes

Reaction equation

HRID 1364460 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@@H:8]2[OH:11])=[CH:4][CH:3]=1.[H-].[Na+].[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18]>CN(C)C=O>[F:14][C:15]1[CH:22]=[CH:21][C:20]([O:11][C@@H:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)[CH2:6][CH2:7]2)=[CH:19][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 28293919HCID 28293919, compound

Product 1

HCID 66924281HCID 66924281, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (S)-6-chloroindan-1-ol (0.45 g, 2.67 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (112 mg, 2.8 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature, stirred for 1 hour. Again, cooled (0° C.), then a solution of 2,6-difluorobenzonitrile (0.41 g, 2.94 mmol) in dimethylfomamide was added, stirred overnight at room temperature. The reaction mixture was poured on crushed-ice water, stirred, filtered, and dried. Purification by silica gel chromatography (dichloromethane) yielded 365 mg of 2-fluoro-5-((S)-6-chloroindan-1-yloxy)benzonitrile.

Workup

  1. temperatureAgain, cooled (0° C.)
  2. stirringstirred overnight at room temperature
  3. additionThe reaction mixture was poured
  4. stirringstirred
  5. filtrationfiltered
  6. customdried
  7. customPurification by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-fb84032398ea45beb4b733ce1c8d47bb
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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