Cyanomethylenetributylphosphorane → Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 923454ノート

反応式

HRID 923454 の反応式
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[C:19]([CH2:24]O)=[N:20][CH:21]=[CH:22][CH:23]=1.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:17][C:18]1[C:19]([CH2:24][O:1][C:2]2[C:3]3[N:4]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 4622928CyanomethylenetributylphosphoraneHCID 19703803(3-Fluoropyridin-2-yl)methanolHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 86718211Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate収率 71.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2 g of ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate, 2 g of (3-fluoropyridin-2-yl)methanol, 4 g of (tributylphosphoranyliden)acetonitrile, and 40 ml of toluene was stirred at 110° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added thereto, and the precipitated solid was collected by filtration. The obtained residue was purified by silica gel column chromatography to obtain 2.15 g of ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration
  4. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8b8173e177f74bd29ba9e7986e33d7a9
出典データセット
uspto-grants-2016_03
特許番号
US09278968B2

反応ノート

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