2-Aminopropanol → 4-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxy-1-methylethyl)aminomethyl]indol-2-yl}isoindolinone

HRID 21036

Reaction equation

HRID 21036 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[NH2:30][CH:31]([CH3:34])[CH2:32][OH:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:30][CH:31]([CH3:34])[CH2:32][OH:33])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Participants

5

Reactant 3

HCID 51262-AminopropanolHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 684925514-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxy-1-methylethyl)aminomethyl]indol-2-yl}isoindolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 56, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (20.0 mg, 0.0487 mmol) was dissolved in dichloromethane (0.5 mL), and the solution was treated with 2-amino-1 propanol (0.0080 mL, 0.10 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) to obtain 4-chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxy-1-methylethyl)aminomethyl]indol-2-yl}isoindolinone.

Sources & evidence

ORD record
ord-8a095a3be3454122832f315b652ab987
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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