Tributylvinyltin → 7-Fluoro-1-trityl-3-vinyl-1H-indazole-5-carbonitrile

HRID 34024Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[C:6]([F:13])[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[CH:33]([Sn](CCCC)(CCCC)CCCC)=[CH2:34]>C1(C)C=CC=CC=1>[F:13][C:6]1[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[C:10]2[C:5]=1[N:4]([C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[N:3]=[C:2]2[CH:33]=[CH2:34]

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen atmosphere, 3.32 g of 3-bromo-7-fluoro-1-trityl-1H-indazole-5-carbonitrile was dissolved in 100 mL of toluene, added with 398 mg of tetrakis(triphenylphosphilne)palladium(0) and 2.50 mL of vinyltributyltin, and stirred at 100° C. for 95 minutes. After cooling to room temperature, 10 g of silica gel was added, the solvent was evaporated, followed by purification by silica gel column chromatography, to afford 2.59 g of the title compound as white crystals.

Workup

temperatureAfter cooling to room temperature
addition10 g of silica gel was added
customthe solvent was evaporated
customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record: ord-865ce43855854fc9a49b8c44a516990f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429609B2

Reaction notes

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