Potassium Hydroxide → HCID 11121794, compound

HRID 2213762Notes

Reaction equation

HRID 2213762 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[OH-].[K+].Cl[C:13]1[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[S:23][C:14]=12>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]3[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[S:23][C:14]=23)=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1819754-Chloro-2-fluorophenolHCID 10824241HCID 10824241, compound

Product 1

HCID 11121794HCID 11121794, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.59 mL (5.5 mmol) of 4-chloro-2-fluorophenol and 100 mg (1.78 mmol) of potassium hydroxide is heated until a homogeneous solution is formed. To this is added 245 mg (1.00 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile and the mixture is heated for 2 hours. Ethyl acetate is added and the solution is washed with 1 N NaOH. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The solid is collected and recrystallized from ethyl acetate to give 195 mg (55%) of a light beige solid, mp 174–175° C.

Workup

  1. temperatureis heated until a homogeneous solution
  2. customis formed
  3. temperaturethe mixture is heated for 2 hours
  4. washthe solution is washed with 1 N NaOH
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid is collected
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-49c47169ece44b1da95554dc08de4314
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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