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

HRID 1661972
Notes
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Reaction equation

HRID 1661972 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f535218efab34905a092a6818ebd2ebd
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes