Potassium Hydroxide → HCID 66897603, compound

HRID 1188921Notes

Reaction equation

HRID 1188921 reaction equation
CS([O:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11]2)(=O)=O.[OH-].[K+]>O1CCCC1.C(O)C.O>[OH:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 86652846HCID 86652846, compound

Product 1

HCID 66897603HCID 66897603, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-[(methylsulfonyl)oxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (11.74 g) was suspended in a mixture of tetrahydrofuran (300 mL) and ethanol (150 mL). A solution of potassium hydroxide (85%, 6.8 g) in water (100 mL) was added to the mixture at 0° C. The mixture was allowed to warm to room temperature and stirred for 12 h. The mixture was concentrated and 1M hydrochloric acid (130 mL) was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (8.39 g, 93%) as a brown solid. MS 349 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. addition1M hydrochloric acid (130 mL) was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-1fa424343f1a451ea7d8fc9e3df35ac3
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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