Sodium Hydroxide → 6-Chloro-1-(2,2-difluoro-ethyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid

HRID 474131Notes

Reaction equation

HRID 474131 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][N:14]([CH2:15][CH:16]([F:18])[F:17])[C:9]2=[CH:8][C:7]=1[Cl:19])=[O:5])C.[OH-].[Na+]>C1COCC1>[Cl:19][C:7]1[CH:8]=[C:9]2[N:14]([CH2:15][CH:16]([F:17])[F:18])[CH:13]=[CH:12][C:10]2=[N:11][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 681085636-Chloro-1-(2,2-difluoro-ethyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 681078206-Chloro-1-(2,2-difluoro-ethyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-chloro-1-(2,2-difluoro-ethyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid ethyl ester (150 mg, 0.520 mmol) in THF (10 ml) was added 1N aq. sodium hydroxide (0.624 ml, 0.624 mmol) and mixture was stirred at 65° C. for 4.5 h. The solvents were evaporated, the residue was dissolved in water, acidified with 2N aq. HCl and the mixture extracted with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated to provide the title compound as light orange solid.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionthe mixture extracted with EtOAc
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-dcd38a14ecb74c18b234daa62917b9a1
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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