Potassium Phosphate, Tribasic → 8-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

HRID 2035609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2035609
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=2)[CH:7]=1.[CH:29]1(B(O)O)[CH2:31][CH2:30]1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Si:22]([O:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([C:8]1[N:6]3[CH:7]=[C:2]([CH:29]4[CH2:31][CH2:30]4)[CH:3]=[CH:4][C:5]3=[N:10][N:9]=1)[CH:20]=[CH:19]2)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 672305262-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline

Produkt 1

HCID 672305218-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolineAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

2-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline (0.500 g, 1.10 mmol), cyclopropylboronic acid (0.123 g, 1.43 mmol), Pd(OAc)2 (0.012 g, 0.0549 mmol), P(Cy)3 (0.031 g, 0.110 mmol), and K3PO4 (0.699 g, 3.29 mmol) were combined with 5.5 mL toluene and 0.55 mL H2O (both degassed with nitrogen 30 minutes prior to use). The mixture was sonicated and put on a 100° C. reaction block and stirred for 3 hours. The reaction mixture was cooled to ambient temperature, diluted with toluene, vacuum filtered through compressed Celite, rinsed with toluene, and the filtrate was concentrated. The crude material was purified on silica (5% to 60% ethyl acetate in dichloromethane) to give the title compound (0.159 g, 0.382 mmol, 34.8% yield) as a brown foam.

Aufarbeitung

  1. customboth degassed with nitrogen 30 minutes
  2. customThe mixture was sonicated
  3. customput on a 100° C.
  4. customreaction block
  5. filtrationfiltered
  6. washrinsed with toluene
  7. concentrationthe filtrate was concentrated
  8. customThe crude material was purified on silica (5% to 60% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-7938f92d242a40d694bc4d7e9b339110
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575145B2

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