Sodium Bicarbonate → HCID 89783433, Verbindung

HRID 58075

Reaktionsgleichung

Reaktionsgleichung von HRID 58075
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH3:15][O:16][C:17]1[N:22]=[CH:21][C:20](B(O)O)=[CH:19][N:18]=1.[C:26]([O-:29])(O)=[O:27].[Na+]>O1CCOCC1.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]>[C:26]([OH:29])([C:11]([F:14])([F:13])[F:12])=[O:27].[CH3:15][O:16][C:17]1[N:22]=[CH:21][C:20]([C:2]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][NH:6]3)=[CH:19][N:18]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 27367782-Methoxypyrimidine-5-boronic acidHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazole

Produkt 2

HCID 6422Trifluoroacetic acidHCID 89783433HCID 89783433, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.377 mmol), (2-methoxypyrimidin-5-yl)boronic acid (0.076 g, 0.491 mmol) and PdCl2(dppf) (0.014 g, 0.019 mmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 35-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 8 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as white solid (0.043 g, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.03 (s, 3H), 7.60 (d, J=1.01 Hz, 1H), 8.00 (s, 1H), 8.34-8.52 (m, 1H), 9.06 (s, 2H); ESI-MS m/z [M+1-1]′ calc'd for C13H9F3N4O, 295.1. found 295.15.

Aufarbeitung

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customthe crude residue was purified by preparative HPLC
  3. washeluting with a gradient of 35-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 8 minutes
  4. customThe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-29f70cdbeb674b7c88130f81f9b812c6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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