Pyridine → HCID 69593693, compound

HRID 1790397Notes

Reaction equation

HRID 1790397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](S(Cl)(=O)=O)=[CH:4][CH:3]=1.C([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21](N)[CH:22]=2)[CH2:17][CH2:16]1)(=O)C.N1C=CC=[CH:27][CH:26]=1>>[F:1][C:2]1[CH:7]=[C:6]([CH:26]=[CH:27][C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:15][CH:16]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 2585641-Acetyl-6-aminoindoline

Product 1

HCID 69593693HCID 69593693, compoundYield 82%

Procedure

Under ice cooling, 4-fluorobenzenesulfonyl chloride (1.4 g) was added dropwise into a solution (10 ml) of 1-acetyl-6-aminoindoline (1.0 g) in pyridine followed by stirring the resultant mixture for 30 min. After concentrating it under reduced pressure, 5 N hydrochloric acid was added thereto and the resultant mixture was heated under reflux for 5 hr. Then the reaction solution was basified with a conc. aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and purified by NH-silica gel column chromatography (methylene chloride/ethanol system) to give the title compound (1.36 g) as white powdery crystals (yield: 82%).

Workup

  1. concentrationAfter concentrating it under reduced pressure, 5 N hydrochloric acid
  2. additionwas added
  3. temperaturethe resultant mixture was heated
  4. temperatureunder reflux for 5 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. custompurified by NH-silica gel column chromatography (methylene chloride/ethanol system)

Sources & evidence

ORD record
ord-d14dd00914d64c3b9ce4a6f342d4f9c1
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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