Triethylamine → HCID 68930524, compound

HRID 34100Notes

Reaction equation

HRID 34100 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][N:8]2[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:31]([O-:33])=[O:32].[CH:34]([C:36]1[CH:44]=[CH:43][C:39]2[O:40][CH2:41][O:42][C:38]=2[CH:37]=1)=[CH2:35].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:40]1[C:39]2[CH:43]=[CH:44][C:36](/[CH:34]=[CH:35]/[C:6]3[C:5]4[C:9](=[CH:10][C:2]([F:1])=[C:3]([N+:31]([O-:33])=[O:32])[CH:4]=4)[N:8]([C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:7]=3)=[CH:37][C:38]=2[O:42][CH2:41]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1389861,3-Benzodioxole, 5-ethenyl-HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68930344HCID 68930344, compound

Product 1

HCID 68930524HCID 68930524, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen atmosphere, 1 g of 6-fluoro-3-iodo-5-nitro-1-trityl-1H-indazole was dissolved in 10 mL of acetonitrile, added successively with 1.35 g of 5-vinyl-benzo[1,3]dioxole, 81.7 mg of palladium acetate (II), 162 mg of 2-(di-tert-butylphosphino)biphenyl and 2 mL of triethylamine, and stirred at 100° C. for 5 hours. After cooling to room temperature, 5 g of silica gel was added, and the solvent was evaporated, and purified by silica gel column chromatography, to obtain 468 mg of the crude product as yellow crystal. This crude product was washed with 50% diethylether solution in hexane, and the solvent was evaporated, to afford 143 mg of the title compound as yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. addition5 g of silica gel was added
  3. customthe solvent was evaporated
  4. custompurified by silica gel column chromatography
  5. customto obtain 468 mg of the crude product as yellow crystal
  6. washThis crude product was washed with 50% diethylether solution in hexane
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-af27b6d4d3c5467d8b3bbf7ae2b1d0c2
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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