Acetic Acid → 4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methoxycarbonylpiperidinomethyl)indol-2-yl]isoindolinone

HRID 21027

Reaction equation

HRID 21027 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[NH:30]1[CH2:38][CH2:37][CH:33]([C:34](N)=[O:35])[CH2:32][CH2:31]1.[C:39](O)(=[O:41])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:30]2[CH2:38][CH2:37][CH:33]([C:34]([O:41][CH3:39])=[O:35])[CH2:32][CH2:31]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 37724-PiperidinecarboxamideHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 684901734-Chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methoxycarbonylpiperidinomethyl)indol-2-yl]isoindolinoneYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (40.0 mg, 0.0974 mmol) was dissolved in acetonitrile (3 mL), and the solution was treated with isonipecotamide (154 mg, 1.20 mmol), acetic acid (0.896 mL, 15.7 mmol) and sodium triacetoxyborohydride (188 mg, 0.887 mmol). The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methoxycarbonylpiperidinomethyl)indol-2-yl]isoindolinone (35.5 mg, yield 70%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4aee51e4bddc4d0fab52a255e6fe7226
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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