Acetic Acid → HCID 86628324, compound

HRID 21305

Reaction equation

HRID 21305 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]N.C1COCC1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:61](#[N:63])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])([CH3:34])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH2:26][N:63]([CH3:61])[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 5

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 66615946Methylamine tetrahydrofuranHCID 86628325HCID 86628325, compound

Product 1

HCID 86628324HCID 86628324, compoundYield 30%

Procedure

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone (0.262 g, 1.17 mmol) was dissolved in acetonitrile (15.0 mL), and the solution was treated with 2.0 mol/L methylamine-THF solution (5.20 mL, 10.5 mmol), acetic acid (0.600 mL, 10.5 mmol) and sodium triacetoxyborohydride (0.555 g, 2.62 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-(dimethylaminomethyl)indol-2-yl]isoindolinone (0.0839 g, 30%).

Workup

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

Sources & evidence

ORD record
ord-7cb3d3707b184f369fa926589fed2f69
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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