3-Fluoro-N-methoxy-N-methylpicolinamide → [4-(Benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone

HRID 573349노트

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HRID 573349 반응식
[F:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:9])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 866889893-Fluoro-N-methoxy-N-methylpicolinamideHCID 178419638HCID 178419638, 화합물

생성물 1

HCID 86688990[4-(Benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide (4.8 g) in THF (100 mL) was added dropwise [4-(benzyloxy)phenyl]magnesium bromide (1 M solution in THF, 27.4 mL) at 0° C. After stirring at 0° C. for 2 h, the mixture was warmed to room temperature and stirred at room temperature overnight. The mixture was quenched with water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (3.0 g).

후처리

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred at room temperature overnight
  3. customThe mixture was quenched with water
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-d857cec3c5e345ac95eab4b94aef57b1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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