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

HRID 331384
ノート
印刷プレビュー

反応式

HRID 331384 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1ff52a3c09cd4beb9d64f0880d28626c
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877747B2

反応ノート

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