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

HRID 34038

Reaction equation

HRID 34038 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:14])=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH2:40])=[CH:37][CH:36]=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([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:7]1[CH:6]=[C:5]2[C:10]([C:2](/[CH:40]=[CH:39]/[C:38]3[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=3)=[N:3][N:4]2[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 689283003-bromo-6-fluoro-5-nitro-1-trityl-1H-indazole

Product 1

HCID 689284926-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-nitro-1-trityl-1H-indazoleYield 46.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 600 mg of 3-bromo-6-fluoro-5-nitro-1-trityl-1H-indazole in 6 mL of N,N-dimethylformamide were successively added 292 mg of 4-fluorostyrene, 71 mg of 2-(di-tert-butylphosphino)biphenyl, 27 mg of palladium acetate (II) and 0.85 mL of triethylamine, and stirred at 80° C. for 6.5 hours. The solvent was evaporated, and the resulting residue was dissolved in 25 mL of ethyl acetate. The organic layer was successively washed with water (twice) and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained crude crystal was recrystallized from ethyl acetate-diisopropylether, to afford 304 mg of the title compound as bright yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in 25 mL of ethyl acetate
  3. washThe organic layer was successively washed with water (twice) and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained crude crystal
  7. customwas recrystallized from ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-3c4fee8c4bba47369bf067c0e1d01924
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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