Sodium hydride → [(6-Chloropyridin-3-yl)methyl](3,4,4-trifluorobut-3-en-1-yl)propanedinitrile

HRID 1795130Notes

Reaction equation

HRID 1795130 reaction equation
[F:1][C:2](=[C:10]([F:12])[F:11])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].[H-].[Na+].Br[CH2:16][C:17]1[CH:18]=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1>CN(C)C=O>[Cl:23][C:20]1[N:19]=[CH:18][C:17]([CH2:16][C:5]([CH2:4][CH2:3][C:2]([F:1])=[C:10]([F:11])[F:12])([C:6]#[N:7])[C:8]#[N:9])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64246615-(Bromomethyl)-2-chloropyridineHCID 22185753(3,4,4-Trifluoro-3-butenyl)malononitrile

Product 1

HCID 22185759[(6-Chloropyridin-3-yl)methyl](3,4,4-trifluorobut-3-en-1-yl)propanedinitrileYield 60.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By using (3,4,4-trifluoro-3-butenyl)malononitrile (0.21 g), N,N-dimethylformamide (5 ml), sodium hydride (60% in oil, 0.05 g) and 3-bromomethyl-6-chloropyridine (0.28 g) according to the similar method described in Production Example 1 was obtained 0.22 g of 2-((6-Chloro-3-pyridyl)methyl)-2-(3,4,4-trifluoro-3-butenyl)malononitrile represented by the following formula (the present invention compound (3)).

Sources & evidence

ORD record
ord-9de10feed80b43d89a9d50af44c63e33
Source dataset
uspto-grants-2006_04
Patent number
US07026340B2

Reaction notes

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