Hydrochloric Acid → HCID 58237057, compound

HRID 1188938Notes

Reaction equation

HRID 1188938 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10]2)[CH3:3].[OH-].[Na+].C(O)C.Cl>O.O1CCCC1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10]2)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 66898273HCID 66898273, compound

Product 1

HCID 58237057HCID 58237057, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (10.7 g), 1M aqueous sodium hydroxide solution (50 mL), ethanol (50 mL) and tetrahydrofuran (50 mL) was stirred at 50° C. for 2 h. 1M Hydrochloric acid (50 mL) was added to the mixture and the mixture was adjusted to pH=6 by 1M aqueous sodium hydroxide solution and water. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound (6.35 g, 64%) as a brown amorphous solid. MS 391 (MH+).

Workup

  1. extractionThe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27da9e37835e4185a13e41f7106b30d0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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