Potassium Hydroxide → HCID 58237054, compound

HRID 1188968Notes

Reaction equation

HRID 1188968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8]2.[OH-].[K+]>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 58236998HCID 58236998, compound

Product 1

HCID 58237054HCID 58237054, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (0.93 g) in tetrahydrofuran (15 mL) and methanol (15 mL) was added a solution of potassium hydroxide (85%, 0.50 g) in water (10 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 yellow amorphous solid, which was crystallized from ethyl acetate-hexane to give the title compound (783 mg, 91%) as pale yellow crystals. MS 362 (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 yellow amorphous solid, which
  8. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d05be44e9c07479290b1725fc98a5c77
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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