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Pyridine → 4-Fluorobenzamide

HRID 1820631
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HRID 1820631 반응식
[N:1]1C=CC=C(OC2C=C(C=C(C#N)C=2)N)C=1.N1C=CC=CC=1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:1])=[O:29])=[CH:26][CH:25]=1
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 22136195HCID 22136195, 화합물

생성물 1

HCID 715724-Fluorobenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1 eq. (0.1 g, 0.473 mmol) of 3-(pyridin-3-yloxy)-5-cyano-aniline in 0.47 M in CH2Cl2 (1 mL) and 1.6 eq. of pyridine (0.56 g, 0.71 mmol) was added 3 eq. of 4-fluorobenzoyl chloride (0.225 g, 1.42 mmol) and the resultant mixture stirred at rt overnight. The reaction mixture was diluted with CH2Cl2, washed with sat. NaHCO3, dried (Na2SO4) and concentrated in vacuo. The resultant residue was diluted with toluene and concentrated in vacuo (5 times). Purification by chromatography over silica with 5% MeOH/CH2Cl2 as the eluant afforded 134 mg of a the desired title compound of Formula I, N-[3-cyano-5-(pyridin-3-yloxy)-phenyl]]-4-fluoro-benzamide, as a solid (85% yield). Mpt 169-172° C. MS (M−1) 332.3.

후처리

  1. washwashed with sat. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. additionThe resultant residue was diluted with toluene
  5. concentrationconcentrated in vacuo (5 times)
  6. customPurification by chromatography over silica with 5% MeOH/CH2Cl2 as the eluant

출처 및 근거

ORD 기록
ord-af2d07cfbdf54b2395b89e1be3477343
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07605164B2

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