Sodium Hydroxide → HCID 11608862, compound

HRID 1631453Notes

Reaction equation

HRID 1631453 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]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]=1[CH3:23]>C1COCC1.CO>[CH2:16]([N:9]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]([CH2:6][C:5]([OH:24])=[O:4])=[C:8]1[CH3:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219482HCID 67219482, compound

Product 1

HCID 11608862HCID 11608862, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (364 μL, 0.364 mmol) is added to a stirring solution of (1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid methyl ester (65 mg, 0.22 mmol) in 5:1 THF/MeOH (2.4 mL). After 5.5 hours, the reaction is evaporated, and partitioned between water and EtOAc. The aqueous layer is acidified to pH 3, and the resulting precipitate collected by filtration to furnish 1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid; MH+=281.

Workup

  1. customthe reaction is evaporated
  2. custompartitioned between water and EtOAc
  3. filtrationthe resulting precipitate collected by filtration
  4. customto furnish 1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid

Sources & evidence

ORD record
ord-3258bc651e034bfba141a08003b20ab1
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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