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Potassium Carbonate → 2'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

HRID 516983
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HRID 516983 반응식
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2].Cl[CH2:21][C:22]1[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=3)=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2]
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6

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HCID 11430Potassium CarbonateHCID 534037442-(Chloromethyl)-3,5-difluoropyridineHCID 1177296262'-Acetyl-3-chloro-4-hydroxy-5'-methyl-[1,4]bipyridinyl-2-one

생성물 1

HCID 1177295302'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

시약·촉매·용매 2

HCID 2855718-Crown-6촉매
HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

To a solution of 2′-acetyl-3-chloro-4-hydroxy-5′-methyl-[1,4′]bipyridinyl-2-one of part D (500 mg, 1.7 mmol) in N,N-dimethylformamide (3 mL) was added 2-chloromethyl-3,5-difluoro-pyridine (277 mg, 1.7 mmol), potassium carbonate (590 mg, 4.28 mmol) and 18-crown-6 (10 mg) and the reaction was stirred at 60° C. for 4 h. After cooling the solution was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide alkylated product as a yellow solid (397 mg): MS (ES) m/e 420 (M+H).

후처리

  1. temperatureAfter cooling the solution
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified

출처 및 근거

ORD 기록
ord-90c3921b347b445b9224ee3d0a6ce4da
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115089B2

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