Acetic Acid → HCID 86628319, compound

HRID 21301Notes

Reaction equation

HRID 21301 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].Cl.[CH3:42][NH:43][CH3:44].C(N(CC)CC)C.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]([CH3:38])([CH3:39])[CH3:37])=[O:34])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH2:31][N:43]([CH3:44])[CH3:42])=[CH:26][CH:25]=3)=[C:16]2[C:12]=1[CH2:13][NH:14][C:15]2=[O:40])(=[O:9])=[O:8]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 86628320HCID 86628320, compound

Product 1

HCID 86628319HCID 86628319, compoundYield 40.1%

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 (0.455 g, 0.807 mmol) was dissolved in acetonitrile (16.0 mL), and the solution was treated with dimethylamine hydrochloride (1.31 g, 16.1 mmol), triethylamine (2.20 mL, 16.1 mmol), acetic acid (0.924 mL, 16.1 mmol) and sodium triacetoxyborohydride (0.513 g, 2.42 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=80/20) to obtain 4-(2-pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone (0.192 g, 40%).

Workup

  1. customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=80/20)

Sources & evidence

ORD record
ord-24240bbe845740abaf32e6d3acc05f69
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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