Acetic Acid → HCID 68490745, compound

HRID 21218Notes

Reaction equation

HRID 21218 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH:21]=O)=[CH:16][CH:15]=3)=[C:8]2[C:4]=1[CH2:5][NH:6][C:7]2=[O:30])[CH3:2].[CH2:31]([CH2:33][NH2:34])[OH:32].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][NH:34][CH2:33][CH2:31][OH:32])=[CH:16][CH:15]=3)=[C:8]2[C:4]=1[CH2:5][NH:6][C:7]2=[O:30])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628291HCID 86628291, compound

Product 1

HCID 68490745HCID 68490745, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-ethyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (68.0 mg, 0.168 mmol) was dissolved in acetonitrile (5.4 mL), and the solution was treated with ethanolamine (0.041 mL, 0.67 mmol), acetic acid (0.192 mL, 3.36 mmol) and sodium triacetoxyborohydride (71.0 mg, 0.336 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with sodium carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-ethyl-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxyethylamino)methyl]indol-2-yl}isoindolinone (72.0 mg, yield 95%).

Workup

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

Sources & evidence

ORD record
ord-e8be07af871d438da7de60c61ce4ae23
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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