Triethylamine → 5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)-ethynyl]nicotinic acid

HRID 391578

Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26].CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:17][N:16]1[C:12]([C:10]([NH:9][C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:20]3[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=3)[C:25]([OH:27])=[O:26])[CH:8]=[CH:7][CH:6]=2)=[O:11])=[CH:13][C:14]([CH3:18])=[N:15]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In a 50 mL round bottom flask, N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (0.888 g, 3.71 mmol) and 5-bromo nicotinic acid (0.50 g, 2.47 mmol) were dissolved in DMF (15 mL) The mixture was then degassed by bubbling N2(g) through it for ˜20 min. The mixture was then treated sequentially with NEt3 (1.37 mL, 9.90 mmol), Pd(PPh3)2Cl2 (0.173 g, 0.247 mmol) and CuI (0.094 g, 4.95 mmol). The reaction mixture was allowed to stir at 50° C. for 4 h. The reaction mixture was diluted with EtOAc (25 mL) causing a pale yellow precipitate to form. The white precipitate was filtered off giving the title compound (0.105 g, 12%).

Aufarbeitung

customwas then degassed
customby bubbling N2(g) through it for ˜20 min
customto form
filtrationThe white precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag: ord-5388f87ef62540f18dbad60e1ebbed8b
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08383825B2

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