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Methanesulfonic Acid → 6-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 2195488
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HRID 2195488 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:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[F:21].[CH2:22]1[CH2:27][O:26][CH:25]=[CH:24][CH2:23]1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:25]2[CH2:24][CH2:23][CH2:22][CH2:27][O:26]2)=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[F:21]
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참가 물질

7

반응물 4

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 667671536-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole

생성물 1

HCID 667669036-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole수율 89%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole (5.0 g, 14.2 mmol) in THF (50 mL) is added DHP (2.4 g, 28.5 mmol) and CH3SO3H (1.0 g, 10.4 mmol). The resulting mixture is stirred at RT for 1 hour. Then EtOAc and aqueous NaHCO3 solutions are added. The organic phase is separated, dried over anhydrous MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (5:1) to give the desired product (5.5 g, 89.0% yield). MS (m/z): 436.0 (M+H).

후처리

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

출처 및 근거

ORD 기록
ord-7ee90691962446b7a97d565705f7a664
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE043878E1

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