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

HRID 923454노트

반응식

HRID 923454 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b8173e177f74bd29ba9e7986e33d7a9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278968B2

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