Acetic Acid → 4-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(methylaminomethyl)indol-2-yl]isoindolinone

HRID 21284

Reaction equation

HRID 21284 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH:22]=O)=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:31].Cl.CN.[CH2:35]([N:37](CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][NH:37][CH3:35])=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:31]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 866282994-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 684894614-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(methylaminomethyl)indol-2-yl]isoindolinoneYield 31.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 6, 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.494 g, 1.17 mmol) was dissolved in acetonitrile (16.0 mL), and the solution was treated with methylamine hydrochloride (1.60 mL, 23.4 mmol), triethylamine (3.30 mL, 23.4 mmol), acetic acid (1.30 mL, 23.4 mmol) and sodium triacetoxyborohydride (0.744 g, 3.51 mmol), followed by purification by flash column chromatography (chloroform/methanol=85/15) to obtain 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(methylaminomethyl)indol-2-yl]isoindolinone (0.159 g, 31%).

Workup

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

Sources & evidence

ORD record
ord-52e2e073909346999c88d97cf12d767c
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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