Sodium Carbonate → 12-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530557
Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[N:30]1[C:34](B(O)O)=[CH:33][CH:32]=[N:31]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[N:30]1[C:34]([C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][CH:15]=2)[C:12]2[N:8]([CH:9]=[C:10]([C:16]4[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=4)[N:11]=2)[CH2:7][CH2:6][O:5]3)=[CH:33][CH:32]=[N:31]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 467394631-(Tetrahydropyran-2-yl)pyrazole-5-boronic acidHCID 582043138-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene

Produkt 1

HCID 6831314112-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaeneAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.00 g, 5.34 mmol), 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-ylboronic acid (1.58 g, 8.01 mmol), Pd(dppf)Cl2 (437 mg, 0.535 mmol), Na2CO3 (1.70 g, 16.0 mmol) in DME/EtOH/H2O (15/3/3 mL) was stirred at 100° C. for 1 hr under microwave irradiation. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and evaporated to give crude product, which was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:5) to afford 12-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.2 g, 90% yield) as white solid. LCMS (ESI) m/z: 446.3 [M+H+].

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with EtOAc/petroleum ether (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-c19389f56872478ab48344a234a42531
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

Notizen zur Reaktion

Wird geladen…