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N-bromobutanimide → Methyl 2-(6-amino-5-bromopyridin-3-yloxy)-4-fluorobenzoate

HRID 1848908
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HRID 1848908 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[Br:20]
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참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 67226188Methyl 2-(6-aminopyridin-3-yloxy)-4-fluorobenzoate

생성물 1

HCID 67226738Methyl 2-(6-amino-5-bromopyridin-3-yloxy)-4-fluorobenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

A mixture of EXAMPLE 318B (1.6 g) in N,N-dimethylformamide (50 mL) was cooled to 0° C., followed by the addition of N-bromosuccinimide (1.195 g) in N,N-dimethylformamide (10 mL) solution. The reaction mixture was stirred at 0° C. for 1 hour, and quenched with ice-cold saturated NaHCO3 aqueous solution. The reaction mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified using flash column purification with 30-40% ethyl acetate/hexane to provide the title compound.

후처리

  1. customquenched with ice-cold saturated NaHCO3 aqueous solution
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified
  8. customflash column purification with 30-40% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-622486f39885432aad9dcadb58df7b4d
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952157B2

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