Boron tribromide → 6-Bromo-1H-indazol-5-ol

HRID 1661970노트

반응식

HRID 1661970 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 569716546-Bromo-5-methoxy-1H-indazole

생성물 1

HCID 591599466-Bromo-1H-indazol-5-ol수율 75.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-bromo-5-methoxy-1H-indazole (60 g, 0.265 mol) in DCM (1300 mL) is added a solution of BBr3 (105 g, 0.42 mol) in DCM (200 mL) at 0° C. The reaction mixture is warmed to RT and stirred overnight. Then the reaction solution is quenched with MeOH at 0° C. The solvent is removed in vacuo and the residue is neutralized with NaHCO3 solid. The mixture is partitioned by water (1500 mL) and EtOAc (1500 mL). The aqueous layer is extracted with EtOAc (1500 mL) two times. The combined organic layers are dried and concentrated to give crude product, which is purified by silica gel column chromatography (PE:THF=2:1) to give the desired product (42.5 g, 75% yield). MS (m/z): 215.0 (M+H).

후처리

  1. customThen the reaction solution is quenched with MeOH at 0° C
  2. customThe solvent is removed in vacuo
  3. customThe mixture is partitioned by water (1500 mL) and EtOAc (1500 mL)
  4. extractionThe aqueous layer is extracted with EtOAc (1500 mL) two times
  5. customThe combined organic layers are dried
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customis purified by silica gel column chromatography (PE:THF=2:1)

출처 및 근거

ORD 기록
ord-b8748961445b471b934da2d17d66348b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030302B2

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