Methyl Acrylate → 3-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl Ester

HRID 8252

Reaktionsgleichung

Reaktionsgleichung von HRID 8252
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=4)=[N:15][N:14]4[CH2:24][CH2:25][CH2:26][C:13]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CCCC)CCCC)CCC.[C:40]([O:44][CH3:45])(=[O:43])[CH:41]=[CH2:42].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C)C=O>[CH3:45][O:44][C:40](=[O:43])[CH:41]=[CH:42][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=4)=[N:15][N:14]4[CH2:24][CH2:25][CH2:26][C:13]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 7294Methyl AcrylateHCID 7622TributylamineHCID 80271Tri-o-tolylphosphine2×HCID 219925227-Bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline

Produkt 1

HCID 666794803-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator2×HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Nitrogen is bubbled through a solution of 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (0.050 g, 0.12 mmol), tributylamine (0.032 mL, 0.17 mmol), methyl acrylate (0.027 mL, 0.24 mmol), and N,N-dimethylformamide (0.5 mL) in toluene (1.0 mL) for 20 min. Pd(OAc)2 (0.002 g, 0.006 mmol) and tri(o-tolyl)phosphine (0.007 g, 0.021 mmol) are added and nitrogen bubbled through the reaction mixture for 10 min. The mixture is heated to 80° C. for 24 h. An additional portion of Pd(OAc)2 (0.002 g, 0.006 mmol) and tri(o-tolyl)phosphine (0.007 g, 0.021 mmol) is added and heating continues for another 24 h. The reaction is cooled and concentrated in vacuo and the residue chromatographed on SiO2 (2% methanol in methylene choloride) to yield the title compound, 0.49 g (97%), as a yellowish solid.

Aufarbeitung

  1. customnitrogen bubbled through the reaction mixture for 10 min
  2. temperatureheating
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on SiO2 (2% methanol in methylene choloride)

Quellen und Nachweise

ORD-Eintrag
ord-e7e385e0055b4b74a462f5b25feca342
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

Verknüpfte Notizen

Wird geladen…