Water → HCID 58306534, compound

HRID 1909901Notes

Reaction equation

HRID 1909901 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[Cl:11])[N:7](C(OC(C)(C)C)=O)[CH:6]=[CH:5]2.O.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[Cl:11])[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 58306778HCID 58306778, compound

Product 1

HCID 58306534HCID 58306534, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-bromo-1-(tert-butoxycarbonyl)-6-chloro-1H-indole-7-carboxylic acid (0.3 g), water (2.0 mL), and methanol (6.0 mL) was added potassium carbonate (0.6 g) at room temperature. The reaction mixture was stirred at 70° C. for 5.5 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added thereto, followed by acidification with 1 M hydrochloric acid. Then, a liquid-separation operation was carried out, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to obtain 5-bromo-6-chloro-1H-indole-7-carboxylic acid (0.22 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere added
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9cc48f31923e46be85c23eb3a8296547
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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