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

HRID 2388982Notes

Reaction equation

HRID 2388982 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-d52d9911576741afac770c8b234b7601
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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