Sodium Hydroxide → HCID 23582408, compound

HRID 1754469Notes

Reaction equation

HRID 1754469 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:21]=[CH:20][O:19][CH:18]=2)[C:8]=1[CH3:22]>C1COCC1.CO>[O:19]1[CH:20]=[CH:21][C:17]([CH2:16][N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:23])=[O:4])=[C:8]2[CH3:22])=[CH:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219284HCID 67219284, compound

Product 1

HCID 23582408HCID 23582408, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (0.25 mL) is added to a stirring solution of (1-furan-3-ylmethyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (7.5 mg, 0.026 mmol) in 1:1 THF/MeOH (1 mL). After 18 hours, the reaction is evaporated and the residue dissolved in water. The aqueous solution is acidified to pH 3-4, and extracted with EtOAc. The organic layer is washed with water then brine, dried (MgSO4), then evaporated to furnish (1-furan-3-ylmethyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid; MH+=271.

Workup

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

Sources & evidence

ORD record
ord-8da787cb6b4e4e0fa25005f7f0bd17ff
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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