Acetic Acid → HCID 86628327, compound

HRID 21307Notes

Reaction equation

HRID 21307 reaction equation
[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH:26]=O)[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:4])=[O:3].[CH3:36][O:37][CH2:38][CH2:39][NH2:40].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH2:26][NH:40][CH2:39][CH2:38][O:37][CH3:36])[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866283254-Methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone

Product 1

HCID 86628327HCID 86628327, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone (0.252 g, 0.503 mmol) was dissolved in acetonitrile (15.0 mL), and the solution was treated with 2-methoxyethylamine (0.875 mL, 10.1 mmol), acetic acid (0.576 mL, 10.1 mmol) and sodium triacetoxyborohydride (0.533 g, 2.52 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=3/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-(2-methoxyethylaminomethyl)indol-2-yl]isoindolinone (0.0968 g, yield 34%).

Workup

  1. customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=3/1)

Sources & evidence

ORD record
ord-ecb75f1794874db49b9b78a7d08ba349
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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