Methanesulfonic Acid → 5-(Benzyloxy)-6-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1661996노트

반응식

HRID 1661996 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[Br:18])[NH:14][N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[Br:18])[N:14]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:19]1)[N:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 667670495-(Benzyloxy)-6-bromo-1H-indazole

생성물 1

HCID 667670665-(Benzyloxy)-6-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole수율 42.3%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 5-(benzyloxy)-6-bromo-1H-indazole (5 g, 16.5 mmol) in THF (30 mL) and DCM (30 mL) is added 3,4-dihydro-2H-pyran (3 mL, 32.8 mmol) and methanesulfonic acid (1 mL, 15.3 mmol). After the reaction mixture is stirred at RT for 2 hours, EtOAc (50 mL) and saturated aqueous NaHCO3 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 give the desired product (2.7 g, 42.2% yield). MS (m/z): 387.0 (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-6cbc3d8fc18a48caa8150b6f171b4adf
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030302B2

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