Sodium Hydroxide → HCID 66898145, compound

HRID 1188924Notes

Reaction equation

HRID 1188924 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][N:18]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][N:18]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66898207HCID 66898207, compound

Product 1

HCID 66898145HCID 66898145, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 7-methoxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (2.78 g) in a mixture of tetrahydrofuran (25 mL) and ethanol (20 mL) was added 1M aqueous sodium hydroxide solution (11 mL), and the mixture was stirred at 50° C. for 40 min. The mixture was concentrated under reduced pressure. The residue was dissolved in water, and 1M hydrochloric acid (11 mL) was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual oil was solidified with diethyl ether to give the title compound (2.18 g, 81%) as a pale orange solid. MS 363 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. addition1M hydrochloric acid (11 mL) was added to the mixture
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fa4604d2986747328b29b7373fc600e0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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