Boron tribromide → HCID 178515912, 화합물

HRID 2183202노트

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HRID 2183202 반응식
[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

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 178489116HCID 178489116, 화합물

생성물 1

HCID 178515912HCID 178515912, 화합물수율 18.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-cdb45e7cdd074d33bc37ce719474f5e8
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897231B2

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