Cesium carbonate → 5-[2-(1,3-Dioxolan-2-yl)ethoxy]-2-fluoropyridine

HRID 1517266노트

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HRID 1517266 반응식
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C(=O)C.[F:21][C:22]1[N:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(OCC)(=O)C.O>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][O:28][C:25]1[CH:24]=[CH:23][C:22]([F:21])=[N:27][CH:26]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 27631086-Fluoropyridin-3-ol

생성물 1

HCID 684307205-[2-(1,3-Dioxolan-2-yl)ethoxy]-2-fluoropyridine수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

2-(2-Bromoethyl)-1,3-dioxolane (2.49 ml, 19.9 mmol) and cesium carbonate (15.1 g, 46.4 mmol) were added to an N,N-dimethylacetamide solution (25 ml) of 6-fluoropyridin-3-ol (1.5 g, 13.3 mmol), and stirred under a nitrogen atmosphere at 100° C. for 12 hours. The reaction solution was cooled with ice, water and ethyl acetate were added, and the organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=5:1 to 1:1) to obtain 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2-fluoropyridine (2.43 g, yield: 86%) as a colorless oil.

후처리

  1. additionwere added
  2. washthe organic layer was washed with water and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=5:1 to 1:1)

출처 및 근거

ORD 기록
ord-06ef82f9cf31447cb63d9866125dd3cc
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232284B2

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