Hydrochloric Acid → HCID 57678934, compound

HRID 491855Notes

Reaction equation

HRID 491855 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[O:22]C(=O)C.[OH-].[K+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[OH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57678943HCID 57678943, compound

Product 1

HCID 57678934HCID 57678934, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Acetic acid 5-bromo-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl ester (20, 150 mg, 0.353 mmol) was added to a stirring solution of 50% potassium hydroxide (2.0 mL) in methanol (6.0 mL). After stirring at 25° C. for 30 min, the reaction mixture was acidified with 1M hydrochloric acid. The organic material was extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford 5-bromo-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-ol (21, 110.0 mg, 81% yield). MS(ESI) [M−H+]−=380.0; 382.0

Workup

  1. extractionThe organic material was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-47783cbef4684107a1712e79ffe159f3
Source dataset
uspto-grants-2009_05
Patent number
US07531568B2

Reaction notes

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