Lithium diisopropylamide → Ethyl 2,6-dichloro-5-fluoro-4-methylnicotinate

HRID 2073821Notes

Reaction equation

HRID 2073821 reaction equation
[Cl:1][C:2]1[N:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:15]([N-]C(C)C)(C)C.[Li+]>>[Cl:1][C:2]1[N:12]=[C:11]([Cl:13])[C:10]([F:14])=[C:9]([CH3:15])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 13210747Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

Product 1

HCID 23364517Ethyl 2,6-dichloro-5-fluoro-4-methylnicotinate

Procedure

Ethyl 2,6-dichloro-5-fluoronicotinate (Chem. Pharm. Bull. 35(6), 2280 (1987)) was treated with lithium diisopropylamide and quenched with methyl iodide to give, upon work-up, ethyl 2,6-dichloro-5-fluoro-4-methylnicotinate. This material was hydrolyzed to give the corresponding acid which was elaborated in the usual manner to give 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid. 7-chloro-1-cyclopropyl-5-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid was synthesized in the same manner.

Workup

  1. customquenched with methyl iodide

Sources & evidence

ORD record
ord-5e2b835698f945b688cba9504f3011cd
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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