Dichloromethane → HCID 58276410, Verbindung

HRID 70334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70334
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[N:8]1)=[O:4].[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>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]>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:21]=[O:22])[CH:28]=3)=[CH:14][CH:13]=2)=[N:8]1)=[O:4]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 58276270HCID 58276270, Verbindung

Produkt 1

HCID 58276410HCID 58276410, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a solution of [3-(4-bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethyl-propanoate (0.108 g, 0.32 mmol; IV-30), 3-formylphenyl boronic acid (0.099 g, 0.66 mmol), and PdCl2(dppf).CH2Cl2 (0.024 g, 0.029 mmol) was added 2M Na2CO3 (aq) (0.38 mL, 0.76 mmol). The mixture was subjected to microwave heating (135° C./50 min), cooled, and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (s, 9 H), 6.10 (s, 2 H), 7.63 (t, J=7.69 Hz, 1 H), 7.73 (d, J=8.06 Hz, 2 H), 7.90 (dd, J=14.65, 7.57 Hz, 2 H), 8.15 (m, 1 H), 8.23 (d, J=8.30 Hz, 2 H), 8.39 (s, 1 H), 10.10 (s, 1 H).

Aufarbeitung

  1. temperaturecooled
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialwere dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3290803bae5044bf80a17e12a7d2ed01
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822518B2

Notizen zur Reaktion

Wird geladen…