Methanol → 7-Ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid

HRID 1188964Notes

Reaction equation

HRID 1188964 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9]2)[CH3:2].O1CCCC1.CO.[OH-].[K+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9]2)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58237028Methyl 7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

Product 1

HCID 582371227-Ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (0.65 g), tetrahydrofuran (10 mL) and methanol (10 mL) was added a solution of potassium hydroxide (85%, 0.33 g) in water (5 mL). The mixture was stirred at room temperature for 15 h and then partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give a light yellow oil, which was crystallized from ethyl acetate-hexane to give the title compound (548 mg, 88%) as pale yellow crystals. MS 377 (MH+).

Workup

  1. custompartitioned between ethyl acetate and aqueous citric acid solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light yellow oil, which
  7. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-521fdbf848084b1c8afba97708a04827
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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