Sodium hydride → 6-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)nicotinonitrile

HRID 1726400Notes

Reaction equation

HRID 1726400 reaction equation
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[H-].[Na+].Cl[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1>CN(C=O)C.O>[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:4][N:5]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178419465HCID 178419465, compound

Product 1

HCID 689208226-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)nicotinonitrileYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 4-(4-bromo-1H-pyrazol-3-yl)-pyridine (200 mg; Example 4, Step 1) in 5 mL DMF was added slowly 0.043 g of a 60% suspension of sodium hydride in mineral oil. After 20 minutes 0.124 g 6-chloronicotinonitrile was added. The mixture was heated at 80° C. overnight. The cooled reaction mixture was diluted with water and resulting solid was collected by vacuum filtration to yield 0.26 g (89% yield) product as a tan solid. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 328.5 by positive ESI.

Workup

  1. customThe cooled reaction mixture
  2. customresulting solid
  3. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-a8ab0e879bea4903ba1506926e57fea6
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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