Sodium Hydroxide → HCID 66726156, compound

HRID 1042129Notes

Reaction equation

HRID 1042129 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([O:23]CC)=[O:22])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([OH:23])=[O:22])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66726217HCID 66726217, compound

Product 1

HCID 66726156HCID 66726156, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (5.6 g) in ethanol (100 mL) and tetrahydrofuran (100 mL) was added 1N aqueous sodium hydroxide solution (31.1 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated, 1N hydrochloric acid (32 mL) was added, and the precipitated crystals were filtered and concentrated under reduced pressure to give the title compound (5.2 g, yield 100%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid (32 mL) was added
  3. filtrationthe precipitated crystals were filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-067da333947848dab98173b318218388
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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