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

HRID 1944443Notes

Reaction equation

HRID 1944443 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:17]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)(=[O:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]1[CH3:32].[OH-].[Li+]>O1CCCC1>[Cl:31][C:27]1[CH:26]=[C:25]([S:22]([C:17]2[C:16]([CH2:15][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[N:5]([CH2:4][C:3]([OH:33])=[O:2])[C:6]=3[CH3:32])=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67044371{3-[2-(3-Chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid methyl ester

Product 1

HCID 58201221{3-[2-(3-Chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {3-[2-(3-chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid methyl ester (0.10 g) and tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.31 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate and the combined extract was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue 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 (0.085 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. extractionthe combined extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue 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-7bf26a7bbf254baea067991c3728f8c8
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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