Triethylamine → 7-Fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1-trityl-1H-indazole-5-carbonitrile

HRID 34025Notes

Reaction equation

HRID 34025 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:32]#[N:33])[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:8]=[C:7]2[CH:30]=[CH2:31].C(N(CC)CC)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.Br[C:63]1[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:32]#[N:33])[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:8]=[C:7]2/[CH:30]=[CH:31]/[C:63]1[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 230701427-Fluoro-1-trityl-3-vinyl-1H-indazole-5-carbonitrile

Product 1

HCID 689303657-Fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1-trityl-1H-indazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Under nitrogen atmosphere, 2.59 g of 7-fluoro-1-trityl-3-vinyl-1H-indazole-5-carbonitrile was dissolved in 50 mL of acetonitrile, added with 10 mL of triethylamine, 271 mg of palladium acetate (II), 450 mg of 2-(di-tert-butylphosphino)biphenyl and 726 μl of 3-bromo pyridine, and refluxed overnight. The solution was cooled to room temperature, added with 10 g of silica gel, the solvent was evaporated, followed by purification by silica gel column chromatography, to afford 2.00 g of the title compound as yellow crystals.

Workup

  1. temperaturerefluxed overnight
  2. additionadded with 10 g of silica gel
  3. customthe solvent was evaporated
  4. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-1481e4fdfcfd4706aab80c7d8c3ca603
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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