Acetic Acid → 4-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone
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.[CH3:33][NH:34][CH3:35].C(N(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]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][N:34]([CH3:35])[CH3:33])=[CH:17][CH:16]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:31]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In a similar manner to Step 2 of Example 6, a crude product of 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.713 g) was dissolved in acetonitrile (20 mL), and the solution was treated with dimethylamine hydrochloride (2.75 g, 33.8 mmol), triethylamine (4.70 mL, 33.8 mmol), acetic acid (1.90 mL, 33.8 mmol) and sodium triacetoxyborohydride (1.10 g, 5.07 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=4/1) to obtain 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone (0.138 g, yield 19%).
Workup
- customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=4/1)
Sources & evidence
- ORD record
- ord-6ff79eed590041f183fc5085a09dd1c8
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745641B2
Reaction notes
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