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Triethylamine → 5-Bromo-6-fluoro-3-[(E)-2-(4-fluorophenyl)vinyl]-1-trityl-1H-indazole

HRID 34131
Notes
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Reaction equation

HRID 34131 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[N:6]=[C:5]2I.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH2:38])=[CH:35][CH:34]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[N:6]=[C:5]2/[CH:38]=[CH:37]/[C:36]1[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 689307235-Bromo-6-fluoro-3-iodo-1-trityl-1H-indazole

Product 1

HCID 689300565-Bromo-6-fluoro-3-[(E)-2-(4-fluorophenyl)vinyl]-1-trityl-1H-indazoleYield 74.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.0 g of 5-bromo-6-fluoro-3-iodo-1-trityl-1H-indazole, 628 mg of 4-fluorostyrene, 115 mg of palladium acetate, 307 mg of 2-(di-ter-butylphosphino)biphenyl and 3.60 mL of triethylamine in N,N-dimethylformamide was stirred at 70° C. for a day. After diluting with ethyl acetate, washing successively with aqueous ammonium chloride and saturated brine, and drying over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:100), to afford 2.2 g of the title compound as colorless crystals.

Workup

  1. washwashing successively with aqueous ammonium chloride and saturated brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:100)

Sources & evidence

ORD record
ord-d6adc56acf8a425a97c316cf88ec27c7
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes