Acetic Acid → HCID 86628322, compound

HRID 21303Notes

Reaction equation

HRID 21303 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([O:10][C:11]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]2[N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH:31]=O)=[CH:26][CH:25]=3)=[C:16]2[C:12]=1[CH2:13][NH:14][C:15]2=[O:40])(=[O:9])=[O:8].[NH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([O:10][C:11]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]2[N:23]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH2:31][N:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)=[CH:26][CH:25]=3)=[C:16]2[C:12]=1[CH2:13][NH:14][C:15]2=[O:40])(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86628320HCID 86628320, compound

Product 1

HCID 86628322HCID 86628322, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-(2-pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.318 g, 0.564 mmol) was dissolved in acetonitrile (10.0 mL), and the solution was treated with piperidine (1.10 mL, 11.3 mmol), acetic acid (0.646 mL, 11.3 mmol) and sodium triacetoxyborohydride (0.359 g, 1.69 mmol), followed by purification by flash column chromatography (chloroform/methanol=85/15) to obtain 4-(2-pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.126 g, 35%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=85/15)

Sources & evidence

ORD record
ord-59e729dc6db14bc9b4aee669c9243629
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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