Boron tribromide → 4-[[5-(4-fluorophenyl)imidazo[4,5-b]pyrazin-3-yl]methyl]phenol

HRID 1297326ノート

反応式

HRID 1297326 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=4)[CH:15]=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)[CH:15]=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 25134Boron tribromide2 回HCID 11151773HCID 11151773、化合物

生成物 1

HCID 113477544-[[5-(4-fluorophenyl)imidazo[4,5-b]pyrazin-3-yl]methyl]phenol収率 88.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-(4-fluoro-phenyl)-1-(4-methoxy-benzyl)-1 H-imidazo[4,5-b]pyrazine (40 mg, 0.12 mmol) in anhydrous dichloromethane (3 mL) at 0° C. was added BBr3 (0.01 mL). The reaction was stirred under nitrogen at 0° C. for 40 minutes, and HPLC showed the presence of 33% of starting material. Another portion of BBr3 (0.01 mL) was added, and the reaction was continued at 0° C. under nitrogen for 2 hours for the completion. The reaction solution was quenched with ice, and partitioned between dichloromethane and water. The organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was purified on a silica gel column eluting with EtOAc-Hexane (1:1) to provide 4-[6-(4-fluoro-phenyl)-imidazo[4,5-b]pyrazin-1-ylmethyl]-phenol as a yellow solid (34 mg).

後処理

  1. waitthe reaction was continued at 0° C. under nitrogen for 2 hours for the completion
  2. customThe reaction solution was quenched with ice
  3. custompartitioned between dichloromethane and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with EtOAc-Hexane (1:1)

出典と根拠

ORDレコード
ord-83e63aa8e3af44888435bb4cb3050b33
出典データセット
uspto-grants-2007_07
特許番号
US07250417B2

反応ノート

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