Potassium Hydroxide → HCID 11121794, compound

HRID 989322Notes

Reaction equation

HRID 989322 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 1N 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 1N 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-780c185b56614aeca7b3b965dceaf535
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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