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Hydrogen Bromide → 3-(3,5-Difluorophenyl)-5-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331384
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HRID 331384 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=3)[C:11](=[O:20])[C:10]=2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Br.[OH-].[Na+]>CC(O)=O>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[C:11](=[O:20])[C:10]=2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:3]=[C:2]([F:1])[CH:7]=1
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참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 703136143-(3,5-Difluorophenyl)-5-methoxy-2-(pyridin-3-yl)-1H-inden-1-one

생성물 1

HCID 703127873-(3,5-Difluorophenyl)-5-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one수율 99.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
120 °C

실험 절차

To a solution of 3-(3,5-difluorophenyl)-5-methoxy-2-(pyridin-3-yl)-1H-inden-1-one (210 mg, 0.60 mmol) obtained in Step 4 in AcOH (6 mL) was added HBr (3 mL). The mixture was heated to reflux at 120° C. for 16 h. The reaction mixture was cooled to room temperature and neutralized with 3N—NaOH. The resulting solution was extracted with EtOAc (10 mL). The extracts were washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by recrystallization with CH2Cl2/hexanes to afford the desired product (200 mg, 99%).

후처리

  1. temperatureThe mixture was heated
  2. extractionThe resulting solution was extracted with EtOAc (10 mL)
  3. washThe extracts were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by recrystallization with CH2Cl2/hexanes

출처 및 근거

ORD 기록
ord-1ff52a3c09cd4beb9d64f0880d28626c
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877747B2

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