Boron tribromide → HCID 178515912、化合物

HRID 2183202ノート

反応式

HRID 2183202 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=5)=[N:20][N:21]=4)[CH:15]=3)[NH:10][N: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[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=5)=[N:20][N:21]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 178489116HCID 178489116、化合物

生成物 1

HCID 178515912HCID 178515912、化合物収率 18.7%

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 round bottom flask containing 1-{5-[3-(4-fluorophenyl)(1H-indazol-5-yl)](4H-1,2,4-triazol-3-yl)]-4-methoxybenzene (100 mg, 0.26 mmol) was added anhydrous dichloromethane (2 ml). The flask, under a nitrogen atmosphere, was placed in an ice/salt bath. To the flask was added boron tribromide (1.3 ml, 1.3 mmol). The reaction was allowed to stir at 0° C. for one hour and at room temperature for an additional four hours. The reaction was quenched with water and the solvent was removed. The product was extracted from the reaction mixture with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated. The product was purified by semipreparative HPLC (20-80% acetonitrile over 30 minutes) to yield the title compound (18 mg, 18.7% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 9.95 (s, 1H), 8.65 (s, 1H), 8.1 (m, 3H), 7.95 (m, 2H), 7.78 (d, 1H), 7.4 (m, 2H), 6.85 (m, 2H), ES-MS m/z 372 [M+H]+.

後処理

  1. customThe flask, under a nitrogen atmosphere, was placed in an ice/salt bath
  2. customThe reaction was quenched with water
  3. customthe solvent was removed
  4. extractionThe product was extracted from the reaction mixture with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by semipreparative HPLC (20-80% acetonitrile over 30 minutes)

出典と根拠

ORDレコード
ord-cdb45e7cdd074d33bc37ce719474f5e8
出典データセット
uspto-grants-2005_05
特許番号
US06897231B2

反応ノート

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