Dimethylamine → Methyl 2-chloro-6-(dimethylamino)-5-fluoronicotinate

HRID 2264328Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][NH:15][CH3:16]>>[Cl:1][C:2]1[N:11]=[C:10]([N:15]([CH3:16])[CH3:14])[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Reactant 2

HCID 674Dimethylamine

HCID 2775354Methyl 2,6-dichloro-5-fluoronicotinate

Product 1

HCID 23112242Methyl 2-chloro-6-(dimethylamino)-5-fluoronicotinate

Procedure

Methyl 2,6-dichloro-5-fluoronicotinate was treated with dimethylamine in a sealed tube to obtain methyl 2-chloro-6-(dimethylamino)-5-fluoronicotinate, which was then reacted under a hydrogen atmosphere in the presence of palladium/carbon to obtain methyl 6-(dimethylamino)-5-fluoronicotinate.

Sources & evidence

ORD record: ord-292c54c6c3c042789f3711f1365d9494
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855198B2

Reaction notes

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