Sodium hydride → 2,2-Dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

HRID 1865645Notes

Reaction equation

HRID 1865645 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:23]([O:29][CH2:30]Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:19])[CH3:20])=[CH:14][CH:13]=3)=[N:9][N:8]([CH2:30][O:29][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 87885Chloromethyl pivalateHCID 178482750HCID 178482750, compound

Product 1

HCID 686621972,2-Dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[4-(5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-phenyl]-dimethyl-amine (500 mg, 1.51 mmol) and N,N-dimethylformamide (40 ml) was stirred at room temperature. Sodium hydride (60%, 121 mg, 3.03 mmol) was added to the mixture, and the reaction mixture was stirred for 30 minutes. Chloromethyl pivalate (0.44 ml, 3.05 mmol) was added, and the reaction mixture was stirred for 1.5 hours at room temperature. Saturated aqueous ammonium chloride solution was added and the mixture extracted with dichloromethane. The crude material was purified by flash chromatography (0 to 100% ethyl acetate in hexanes) to give 517 mg (77%) of 2,2-dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester. MS m/z 445.2, 447.2 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred for 1.5 hours at room temperature
  2. extractionthe mixture extracted with dichloromethane
  3. customThe crude material was purified by flash chromatography (0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f6b6bce3c05543d78ba1fb344eb2b6f7
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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