Tri-o-tolylphosphine → 4-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile
Reaktionsgleichung
Br[C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[F:18])=[N:4][N:5]([CH3:9])[C:6]=1[C:7]#[N:8].C([Sn](CCCC)(CCCC)[C:24]1[C:28]([CH3:29])=[CH:27][S:26][C:25]=1[CH3:30])CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH3:30][C:25]1[S:26][CH:27]=[C:28]([CH3:29])[C:24]=1[C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[F:18])=[N:4][N:5]([CH3:9])[C:6]=1[C:7]#[N:8]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
4-bromo-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (49 mg, 0.16 mmol), tributyl(2,4-dimethylthiophen-3-yl)stannane (82.24 mg, 0.20 mmol), Pd2(dba)3 (14.44 mg, 0.02 mmol) and trio-tolylphosphine (9.6 mg, 0.03 mmol) were mixed with 1.5 mL DMF and the mixture was degassed under nitrogen in a vial. The vial was sealed and the reaction was heated at 85° C. over night. Water was added, the mixture was extracted with CH2Cl2 and the organic layer was concentrated. The crude product was purified on silica to give 4-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (17 mg, 32%).
Aufarbeitung
- customthe mixture was degassed under nitrogen in a vial
- customThe vial was sealed
- additionWater was added
- extractionthe mixture was extracted with CH2Cl2
- concentrationthe organic layer was concentrated
- customThe crude product was purified on silica
Quellen und Nachweise
- ORD-Eintrag
- ord-5fc8ea61b33942af830af66b15820a09
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08653112B2
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