Cesium carbonate → Ethyl 2-[3-(ethylsulfanyl)phenoxy]-5-fluoronicotinate

HRID 724284ノート

反応式

HRID 724284 の反応式
Cl[C:2]1[N:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14]([S:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:7]([O:6][C:4](=[O:5])[C:3]1[CH:9]=[C:10]([F:13])[CH:11]=[N:12][C:2]=1[O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([S:16][CH2:14][CH3:15])[CH:18]=1)[CH3:8]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 11390082Ethyl 2-chloro-5-fluoronicotinateHCID 129052213-(Ethylsulfanyl)phenol

生成物 1

HCID 21877167Ethyl 2-[3-(ethylsulfanyl)phenoxy]-5-fluoronicotinate収率 15%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Ethyl 2-chloro-5-fluoro-nicotinate (J. Med. Chem. 1993, 36, 2676, M. Winn et. al.) (5.0 g, 24 mmol), 3-ethylsulfanylphenol (3.8 g, 24 mmol) and caesium carbonate (7.98 g, 24 mmol) were suspended in dioxan (50 ml) and the reaction was heated to 100° C. and stirred at this temperature under nitrogen for 8 h. The reaction was cooled to room temperature, filtered and the solid washed with ethyl acetate (50 ml). The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5) to give 5-fluoro-2-(3-ethylsulfanyl-phenoxy)-nicotinic acid ethyl ester (1.16 g).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. washthe solid washed with ethyl acetate (50 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5)

出典と根拠

ORDレコード
ord-2a1db452f43a4da3b881fa7b3b936d8a
出典データセット
uspto-grants-2006_11
特許番号
US07141586B2

反応ノート

読み込み中…