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Dimethylformamide → 3-[(3-Chlorophenyl)methoxy]pyridin-2-amine

HRID 1622852
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HRID 1622852 반응식
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CN(C=O)C.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1>CCOC(C)=O.O>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][O:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 281142-Amino-3-HydroxypyridineHCID 698381-(Bromomethyl)-3-chlorobenzene

생성물 1

HCID 103540293-[(3-Chlorophenyl)methoxy]pyridin-2-amine수율 94.8%

시약·촉매·용매 2

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To the mixture of 2-aminopyridin-3-ol (500 mg) and DMF (dry) (15 mL) was added NaH (60%, 200 mg) at room temperature and the mixture was stirred at room temperature for 20 min. 1-(Bromomethyl)-3-chlorobenzene (933 mg) was added and the mixture was stirred at the same temperature for 1 hr. Water and EtOAc were added and the extracted organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (1.01 g) as a brown crystalline solid.

후처리

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. washthe extracted organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

출처 및 근거

ORD 기록
ord-e392bc1209fe45e2afed66d1381b74b7
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778934B2

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