3-Bromopyridine → 4-Methoxy-3-[(E)-2-(pyridin-3-yl)-vinyl]-1-trityl-1H-indazole-5-carbonitrile

HRID 34047

Reaktionsgleichung

[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]#[N:15])[C:10]=2[O:12][CH3:13])[N:5]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1)=[CH2:2].Br[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1.C1(C)C=CC(P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][O:12][C:10]1[C:9]([C:14]#[N:15])=[CH:8][CH:7]=[C:6]2[C:11]=1[C:3](/[CH:1]=[CH:2]/[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)=[N:4][N:5]2[C:16]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

300 mg of 3-vinyl-4-methoxy-1-trityl-1H-indazole-5-carbonitrile and 180 μl of 3-bromopyridine were dissolved in a mixed solvent of 1 mL triethylamine/5 mL acetonitrile, added with 40 mg of tri-p-tolylphosphine and 27 mg of palladium acetate (II), and heated at 110° C. for 24 hours. The reaction solution was added with silica gel, the solvent was evaporated, and the resultant residue was purified by column chromatography (hexane:ethyl acetate=7:3), to afford 120 mg of the title compound as a pale yellow oil.

Aufarbeitung

additionThe reaction solution was added with silica gel
customthe solvent was evaporated
customthe resultant residue was purified by column chromatography (hexane:ethyl acetate=7:3)

Quellen und Nachweise

ORD-Eintrag: ord-4110f144624145549fb126ad24035122
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07429609B2

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