Lithium Hydroxide → {5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)pyridin-2-ylmethyl]-2-methylindol-1-yl}acetic acid

HRID 1944396Notes

Reaction equation

HRID 1944396 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[C:21]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:6]1[CH3:32].[OH-].[Li+]>O1CCCC1>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]([OH:33])=[O:2])[C:6]([CH3:32])=[C:7]2[CH2:15][C:16]1[C:21]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67044579{5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)pyridin-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester

Product 1

HCID 42644621{5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)pyridin-2-ylmethyl]-2-methylindol-1-yl}acetic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {5-fluoro-3-[3-(4-fluorobenzenesulfonyl)pyridin-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester (0.18 g) in tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.45 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume) to afford the title compound as a white solid (0.13 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionpH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume)

Sources & evidence

ORD record
ord-d82c01621d1f4fc99376c0ab47c3d62f
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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