Potassium Hydroxide → HCID 59409531, compound

HRID 659955Notes

Reaction equation

HRID 659955 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=2)=[CH:4][CH:3]=1.[OH-:25].[K+]>C(O)(C)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:24])=[O:25])[CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68430447HCID 68430447, compound

Product 1

HCID 59409531HCID 59409531, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1.44 g (4.6 mmoles) of 4-[3-(4-Fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridine-2-carbonitrile is stirred at room temperature in 8 mL of t-butanol in the presence of 1.03 g (18.3 mmoles) of powdered potassium hydroxide. The reaction is stirred at room temperature for 4 hours, concentrated under vacuum and poured into water and ethyl acetate (1/1). Chlorhydric acid 2N is added to the solution to reach pH=5 and the solution is extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration 800 mg of 4-[3-(4-Fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridine-2-carboxylic acid amide are obtained as white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. additionpoured into water and ethyl acetate (1/1)
  3. additionChlorhydric acid 2N is added to the solution
  4. extractionthe solution is extracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-50ed1e255d8c468bbe9f8e6a230328cb
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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