Dimethylformamide → 2-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)benzaldehyde

HRID 640361

반응식

HRID 640361 반응식
CN(C)C=O.[F:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[H-].[Na+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1>O>[F:6][C:7]1[CH:14]=[C:13]([O:15][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5872462-Fluoro-4-hydroxybenzaldehydeHCID 216980592-(Chloromethyl)-5-fluoropyridine

생성물 1

HCID 592553562-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)benzaldehyde수율 42.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an N,N-dimethylformamide (20.0 mL) solution of 2-fluoro-4-hydroxy-benzaldehyde (1.48 g, 10.2 mmol) was added sodium hydride (411 mg, 10.3 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 20 minutes at room temperature. 2-Chloromethyl-5-fluoro-pyridine (1.20 g, 8.56 mmol) described in Manufacturing Example 41-1-2 was then added at room temperature, and stirred for 30 minutes at 80° C. Water was added at room temperature to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5→1:2) to obtain the title compound (901 mg, 42.2%).

후처리

  1. additionwas then added at room temperature
  2. stirringstirred for 30 minutes at 80° C
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5→1:2)

출처 및 근거

ORD 기록
ord-509b35bb32cb415187b898623294edf1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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