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

HRID 1517266ノート

反応式

HRID 1517266 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-06ef82f9cf31447cb63d9866125dd3cc
出典データセット
uspto-grants-2012_07
特許番号
US08232284B2

反応ノート

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