Potassium Carbonate → 3-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

HRID 1831915

반응식

HRID 1831915 반응식
[Br:1][C:2]1[C:3](=[O:18])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].C([O-])([O-])=O.[K+].[K+].[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][CH:28]=1>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[C:3](=[O:18])[N:4]([CH2:33][C:30]2[CH:31]=[CH:32][C:27]([CH2:26][Cl:25])=[CH:28][CH:29]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 220508323-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

생성물 1

HCID 220500273-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one수율 43.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
110 °C

실험 절차

To a solution of 3-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one (0.60 g, 2.5 mmol) in DMF (40 mL) was added K2CO3 (0.70 g, 5.1 mmol) and α,α′-dichloro-p-xylene (0.53 g, 3.0 mmol), and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with brine, and extracted with CHCl3 (4×100 mL). The combined organics were washed water and then brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 3-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one as an off-white solid (0.49 g, 43%): 1H NMR (300 MHz, CDCl3) δ 7.54 (app q, J=8 Hz, 1H), 7.38-7.28 (m, 5H), 6.94 (td, J=8, 2 Hz, 1H), 6.85 (td, J=8, 2 Hz, 1H), 6.10 (d, J=9 Hz, 1H), 5.21 (s, 2H), 5.16 (s, 2H), 4.56 (s, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with CHCl3 (4×100 mL)
  3. washThe combined organics were washed water
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4e28755e94ff450a8b2e38b4451c5d4e
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067540B2

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