Sodium hydride → 6-(3,3-Dimethyl-1-oxo-indan-5-yloxy)nicotinonitrile

HRID 747953Notes

Reaction equation

HRID 747953 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][C:7]2([CH3:15])[CH3:14].Cl[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=1>CS(C)=O>[CH3:14][C:7]1([CH3:15])[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([O:3][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=3)[CH:5]=2)[C:9](=[O:13])[CH2:8]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 13714036HCID 13714036, compound

Product 1

HCID 666728106-(3,3-Dimethyl-1-oxo-indan-5-yloxy)nicotinonitrileYield 70.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Add NaH (60%/oil, 196 mg, 4.91 mmol) to a mixture of 5-hydroxy-3,3-dimethyl-1-indanone (787 mg, 4.46 mmol) and DMSO (10 ml) stirring at ambient temperature under nitrogen. After ten minutes, add 6-chloronicotinonitrile (619 mg, 4.46 mmol) dissolved in DMSO (10 ml) and stir the resulting mixture at 60° C. overnight. Quench the reaction with saturated aqueous NH4Cl and extract with EtOAc (2×). Wash extract with water and brine, dry (MgSO4) and concentrate on rotary evaporator to a brown, oily solid. Purify on silica gel (10% EtOAc/DCM) to give 877 mg of 6-(3,3-Dimethyl-1-oxo-indan-5-yloxy)-nicotinonitrile as a yellow solid.

Workup

  1. waitAfter ten minutes
  2. stirringstir the resulting mixture at 60° C. overnight
  3. customQuench
  4. customthe reaction with saturated aqueous NH4Cl
  5. extractionextract with EtOAc (2×)
  6. washWash
  7. extractionextract with water and brine
  8. dry with materialdry (MgSO4)
  9. concentrationconcentrate on rotary evaporator to a brown, oily solid
  10. customPurify on silica gel (10% EtOAc/DCM)

Sources & evidence

ORD record
ord-b51e6e8bb91b4c849917d086e5f97172
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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