Sodium Hydroxide → HCID 11608862, compound

HRID 1445564Notes

Reaction equation

HRID 1445564 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-267673784dfe4445ade16b58ec443ab2
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

Loading…