Benzyl Alcohol → 5-(Benzyloxy)-6-bromo-1H-indazole

HRID 1661995노트

반응식

HRID 1661995 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[OH:11].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:12]([O:11][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Br:1])[NH:8][N:7]=[CH:6]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 5

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5462977Diethyl azodicarboxylateHCID 591599466-Bromo-1H-indazol-5-ol

생성물 1

HCID 667670495-(Benzyloxy)-6-bromo-1H-indazole수율 70.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 6-bromo-5-hydroxy-1H-indazole (5 g, 23.5 mmol) in THF (50 mL) is added benzyl alcohol (3.05 g, 28.2 mmol), PPh3 (7.39 g, 28.2 mmol) and diethylazodicarboxylate (4.46 mL, 28.2 mmol). After the reaction mixture is stirred at RT overnight, EtOAc (50 mL) and saturated aqueous NH4Cl (30 mL) are added. The organic phase is separated, dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (4:1) to provide the product (5.0 g, 70.2% yield). MS (m/z): 303.0 (M+H).

후처리

  1. customThe organic phase is separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel column chromatography
  5. washeluting with PE

출처 및 근거

ORD 기록
ord-808a9cc82f2145129a401af8e37a52d8
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030302B2

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