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

HRID 1866921노트

반응식

HRID 1866921 반응식
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:26]=1[CH2:27]Br>CC(C)=O>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:27][C:26]1[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:25]=1[F:24]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724177HCID 54724177, 화합물

생성물 1

HCID 102165503-bromo-4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one (0.20 g, 0.67) and K2CO3 (0.27 g, 1.34 mmol) in acetone (10 mL) was added 2,4-difluorobenzyl bromide (0.16 g, 0.8 mmol), and the reaction mixture was heated at reflux for 1 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with water and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure. 1H NMR (300 MHz, CDCl3) δ 7.65-7.55 (m, 1H), 7.40-7.25 (m, 2H), 7.15-6.80 (m, 5H), 6.14 (d, J=8 Hz, 1H), 5.22 (s, 2H), 5.16 (s, 2H). ESHRMS m/z 424.0159 (M+H C19H14BrF3NO2 requires 424.0155).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic solution was washed with water
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f04d79d86b5d48a681153b214a703a34
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629363B2

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