Sodium Carbonate → HCID 118046190, Verbindung

HRID 596066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596066
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.F[CH:29](F)[N:30]1[CH:34]=[C:33](I)[C:32](C)=[N:31]1.C([O-])([O-])=O.[Na+].[Na+].[O-]S([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].CCOC(C)=O.COCCOC>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([C:33]2[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=2)=[CH:4][N:3]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 463183071-(Difluoromethyl)-4-iodo-3-methyl-1H-pyrazoleHCID 123330616HCID 123330616, Verbindung

Produkt 1

HCID 118046190HCID 118046190, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of crude methyl 4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2-fluorobenzoate (712 mg, 1.912 mmol), 1-(difluoromethyl)-4-iodo-3-methyl-1H-pyrazole (740 mg, 2.87 mmol), PdCl2(dppf) (70.0 mg, 0.096 mmol), DME (7.899 mL), and 2M Na2CO3 (3.95 mL) was heated at 100° C. overnight. After adding Na2SO4 followed by dilution with EtOAc, the reaction mixture was filtered off and the resulting volatile materials were concentrated in vacuo. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc in DCM. LCMS (m/z): 491.1 (MH+), 0.64 min

Aufarbeitung

  1. filtrationthe reaction mixture was filtered off
  2. concentrationthe resulting volatile materials were concentrated in vacuo
  3. customThe crude product was purified by flash chromatography
  4. washeluting with 0-100% of EtOAc in DCM
  5. custom491.1 (MH+), 0.64 min

Quellen und Nachweise

ORD-Eintrag
ord-82a1d98e52b84479b39aa76c01f42891
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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