Potassium Carbonate → HCID 66673442, compound

HRID 747956Notes

Reaction equation

HRID 747956 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[C:9]([CH3:18])=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11]2.Cl[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=1>CS(C)=O>[CH3:18][C:9]1[C:8]([O:7][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 666729025-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 66673442HCID 66673442, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add K2CO3 (1.24 g, 9.00 mmol) to a mixture of 5-hydroxy-4-methyl-1-indanone (973 mg, 6.00 mmol), 6-chloronicotinonitrile (831 mg, 6.00 mmol) and DMSO (15 ml) stirring at ambient temperature under nitrogen. Heat the mixture at 55° C. for three days. 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 foam. Purify on silica gel (10% EtOAc/DCM) to give 1.22 g of 6-(4-Methyl-1-oxo-indan-5-yloxy)-nicotinonitrile as a yellow solid.

Workup

  1. temperatureHeat the mixture at 55° C. for three days
  2. customQuench
  3. customthe reaction with saturated aqueous NH4Cl
  4. extractionextract with EtOAc (2×)
  5. washWash
  6. extractionextract with water and brine
  7. dry with materialdry (MgSO4)
  8. concentrationconcentrate on rotary evaporator to a brown foam
  9. customPurify on silica gel (10% EtOAc/DCM)

Sources & evidence

ORD record
ord-50983e424dce4805b903933d23c97d16
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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