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Triethylamine → {3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl Ester

HRID 34110
Notes
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Reaction equation

HRID 34110 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](I)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH2:44])=[CH:41][CH:40]=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>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](/[CH:44]=[CH:43]/[C:42]3[CH:45]=[CH:46][C:39]([F:38])=[CH:40][CH:41]=3)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68926908(3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic Acid Tert-Butyl Ester

Product 1

HCID 68931002{3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl Ester
Yield 68.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a solution of 400 mg of (3-iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic acid tert-butyl ester and 162 mg of 4-fluorostyrene in 2.0 mL of N,N-dimethylformamide were added 15 mg of palladium acetate, 40 mg of 2-(di-tert-butylphosphino)biphenyl and 0.46 mL of triethylamine at room temperature, and stirred at 80° C. for 6 hours. After diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3). The resultant crystals were washed with diethyl ether, to afford 270 mg of the title compound as colorless crystals.

Workup

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3)
  6. washThe resultant crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-5bc733d0f6204d94be8247f1050b8975
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes