Methanol → HCID 58236987, compound

HRID 1188959Notes

Reaction equation

HRID 1188959 reaction equation
[F:1][C:2]1[C:10]([O:11]S(C)(=O)=O)=[C:9]2[C:5]([CH:6]=[C:7]([C:16]([O:18]CC)=[O:17])[NH:8]2)=[CH:4][C:3]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=1.O1CCCC1.CO.[OH-].[K+]>O>[F:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH:6]=[C:7]([C:16]([OH:18])=[O:17])[NH:8]2)=[CH:4][C:3]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58237123HCID 58237123, compound

Product 1

HCID 58236987HCID 58236987, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 6-fluoro-7-[(methylsulfonyl)oxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (3.1 g), tetrahydrofuran (25 mL) and methanol (25 mL) was added a solution of potassium hydroxide (85%, 1.9 g) in water (15 mL). The mixture was stirred at room temperature for 15 h and then concentrated in vacuo. The residue was 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 pink solid, which was washed with ethyl acetate-hexane to give the title compound (2.52 g, 100%) as a light pink solid. MS 365 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and aqueous citric acid solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a light pink solid, which
  8. washwas washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-9889ef5d2215480aa87490a2d99da303
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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