1-(4-Pyridyl)piperazine → 4-Chloro-7-(1-(tert-butoxycarbonyl)-5-[4-(pyridin-4-yl)piperazin-1-ylmethyl]indol-2-yl)isoindolinone

HRID 21059Notes

Reaction equation

HRID 21059 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].[N:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1.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]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:39]2[CH2:40][CH2:41][N:36]([C:33]4[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=4)[CH2:37][CH2:38]2)=[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 705171-(4-Pyridyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 684952684-Chloro-7-(1-(tert-butoxycarbonyl)-5-[4-(pyridin-4-yl)piperazin-1-ylmethyl]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). The solution was treated with 1-(pyridin-4-yl)piperazine (32 mg, 0.20 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)-5-[4-(pyridin-4-yl)piperazin-1-ylmethyl]indol-2-yl)isoindolinone.

Sources & evidence

ORD record
ord-c5e9bf1cab694fb8ba3d72a4399b3347
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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