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Methyl iodide → N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide

HRID 2380238
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HRID 2380238 반응식
[H-].[Na+].[Br:3][C:4]1[C:9]([NH:10][C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=1.[CH3:22]I>CS(C)=O>[Br:3][C:4]1[C:9]([N:10]([CH3:22])[C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10617311N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide

생성물 1

HCID 10737014N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
50 °C

실험 절차

Sodium hydride (0.3 g of a 50% dispersion in mineral oil) was added to dimethylsulfoxide (10 ml) and warmed to 50° C. After cooling the mixture to room temperature. N-(2-bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide (2.0 g) was added and the resulting solution was stirred for 10 min. Methyl iodide (0.4 ml) was then added and the mixture was stirred for 30 min. The reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml) was then added. The organic phase was washed with water (4×100 ml), dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2) to give 1.9 g of the title compound, suitable for use in the next reaction.

후처리

  1. temperatureAfter cooling the mixture to room temperature
  2. stirringthe mixture was stirred for 30 min
  3. customThe reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml)
  4. additionwas then added
  5. washThe organic phase was washed with water (4×100 ml)
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2)

출처 및 근거

ORD 기록
ord-0ea599a957014569abf45d76d00040de
출처 데이터셋
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05366972

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