Dimethylformamide → 2-(1-Cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyridine

HRID 1666544노트

반응식

HRID 1666544 반응식
[H-].[Na+].[CH:3]1([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.F[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)=[CH:23][N:22]=1>O>[CH:3]1([N:8]2[CH2:9][CH2:10][CH:11]([O:14][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)=[CH:23][N:22]=3)[CH2:12][CH2:13]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 217027851-Cyclopentylpiperidin-4-olHCID 231159914-(6-Fluoropyridin-3-yl)benzonitrile

생성물 1

HCID 113024522-(1-Cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyridine

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

60% sodium hydride (13 mg) and 1-cyclopentyl-4-hydroxypiperidine (60 mg) were added to a DMF solution (3 ml) of 2-fluoro-5-[4-cyanophenyl]pyridine (56 mg), and stirred at 130° C. for 7 hours. The reaction mixture was cooled to room temperature, and water was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1) to obtain the entitled compound.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1)
  7. customto obtain the entitled compound

출처 및 근거

ORD 기록
ord-f5e246c79d2a48bbab46721a125a7a27
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044070B2

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