Dimethylformamide → HCID 23157487, compound

HRID 508003Notes

Reaction equation

HRID 508003 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 23157487HCID 23157487, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxyindan-1-one (2.94 g, 19.8 mmol), 2-chloro-5-(trifluoromethyl)pyridine (3.00 g, 16.5 mmol), potassium-carbonate (6.84 g, 49.5 mmol) and N,N-dimethylformamide (40 mL) was stirred under a nitrogen atmosphere at 100° C. for 8 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-hexane/ethyl acetate=60/40) to give the title compound (2.74 g, yield 69%) as pale-yellow crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-hexane/ethyl acetate=60/40)

Sources & evidence

ORD record
ord-7971e88357f6496b85478ab07b5f8c95
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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