Hydrochloric Acid → HCID 68184271, compound

HRID 878983Notes

Reaction equation

HRID 878983 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][C:18]([OH:20])=[O:19])[CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21]N1C(=O)CCC1=O.Cl>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][C:18]([OH:20])=[O:19])[CH:15]=2)[C:10]([Cl:21])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 544889242-(1-benzyl-1H-indole-6-yl)acetic acid

Product 1

HCID 68184271HCID 68184271, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound [4] obtained in Example 4 (82 mg) in tetrahydrofuran (1 mL) was added N-chlorosuccinimide (26 mg) at room temperature, and then the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 4N-hydrochloric acid for acidification, and then extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (19 mg) as a red solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b4b6c1b9df964f1aaa8bd2e520a1fa38
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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