Water → HCID 86628238, compound

HRID 21133Notes

Reaction equation

HRID 21133 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C(N(CC)CC)C.[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[C:45]([F:53])[CH:44]=1.O>C(#N)C>[F:53][C:45]1[CH:44]=[C:43]([Cl:42])[CH:48]=[CH:47][C:46]=1[S:49]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34])(=[O:51])=[O:50]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27788604-Chloro-2-fluorobenzene-1-sulfonyl chlorideHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 86628238HCID 86628238, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0300 g, 0.0650 mmol) was dissolved in acetonitrile (0.650 mL), and the solution was added with triethylamine (0.0540 mL, 0.390 mmol) and 4-chloro-2-fluorobenzenesulfonyl chloride (0.0450 g, 0.195 mmol), followed by stirring at room temperature for 12 hours. The reaction mixture was added with water and the solvent was evaporated. The residue was added with water and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then filtered through a column filled with SCX (positive-ion exchange resin). The SCX was washed with 2 mol/L ammonia-methanol solution and the filtrate was evaporated to obtain 4-(2-fluoro-4-chlorobenzenesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0116 g, yield 27%).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was added with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered through a column
  7. additionfilled with SCX (positive-ion exchange resin)
  8. washThe SCX was washed with 2 mol/L ammonia-methanol solution
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-687c5da3aade418696d9ded1a9b815e7
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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