Dimethylformamide → 4-(3-Fluoro-pyridin-2-yloxymethyl)-benzaldehyde

HRID 640431노트

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HRID 640431 반응식
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[F:19][C:18]1[C:13]([O:12][CH2:11][C:10]2[CH:20]=[CH:21][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 592552352-(4-Bromo-benzyloxy)-3-fluoro-pyridineHCID 178418339Butyllithium

생성물 1

HCID 592552614-(3-Fluoro-pyridin-2-yloxymethyl)-benzaldehyde수율 53%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-78 °C

실험 절차

To a tetrahydrofuran (40 mL) solution of 2-(4-bromo-benzyloxy)-3-fluoro-pyridine (2.03 g, 7.20 mmol) described in Manufacturing Example 149-1-1 was added n-Butyl lithium (5.04 mL, 1.6 M hexane solution, 7.92 mmol) under nitrogen atmosphere at −78° C., which was stirred for 45 minutes at −78° C. Then, N,N-dimethylformamide (725 μL, 9.36 mmol) was added to the reaction mixture at −78° C., which was stirred for 1 hour and 10 minutes while the temperature was raised to room temperature. Water was added to the reaction solution at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (887 mg, 53%).

후처리

  1. stirringwhich was stirred for 1 hour and 10 minutes while the temperature
  2. temperaturewas raised to room temperature
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-824a6ae5635e4b33942f6da94baf41c3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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