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

HRID 1081398ノート

反応式

HRID 1081398 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

Ethyl 2,6-dichloro-5-fluoronicotinate (Chem. Pharm. Bull. 3.5.(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.

後処理

  1. customquenched with methyl iodide

出典と根拠

ORDレコード
ord-7f37056c1c3446458496b1dc5128cf8d
出典データセット
uspto-grants-1996_12
特許番号
US05585491

反応ノート

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