Acetic Acid → HCID 68487468, compound

HRID 21029

Reaction equation

HRID 21029 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[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[CH2:36][OH:37].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]2[CH2:36][OH:37])=[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 313Hydrochloric AcidHCID 94263Piperidin-2-ylmethanolHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 68487468HCID 68487468, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (50.9 mg, 0.124 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 2-piperidine methanol (63.8 mg, 0.554 mmol), acetic acid (0.284 mL, 4.96 mmol) and sodium triacetoxyborohydride (158 mg, 0.745 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and ethyl acetate, followed by extracting with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium hydrogen 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-[2-(hydroxymethyl)piperidinomethyl]indol-2-yl}isoindolinone (36.2 mg, yield 57%).

Workup

  1. extractionby extracting with 1 mol/L hydrochloric acid
  2. additionThe aqueous layer was added with sodium hydrogen carbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4088332286f84ac9aff0f3cedb317183
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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