Sodium Hydroxide → [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1754465Notes

Reaction equation

HRID 1754465 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:24])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:8]=1[CH3:23]>C1COCC1.CO>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:24])=[O:4])=[C:8]2[CH3:23])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67220030[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 11709219[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (0.5 mL) is added to a stirring solution of [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (4 mg, 0.013 mmol) in 1:1 THF/MeOH (2 mL). After 18 hours, the reaction is evaporated and the residue dissolved in water. The aqueous solution is acidified to pH 1, and extracted with ethyl acetate. The organic layer is washed with water then brine, dried (MgSO4) then evaporated, to give [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid; MH+=301.

Workup

  1. customthe reaction is evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customthen evaporated

Sources & evidence

ORD record
ord-158172bf85b74b8fb85ff028b91c73c1
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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