Sodium Bicarbonate → Trifluoroacetic acid

HRID 58039

Reaktionsgleichung

Reaktionsgleichung von HRID 58039
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.CC1(C)C(C)(C)OB([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([C:29]([O:31]C)=[O:30])[CH:24]=2)O1.[C:34]([O-:37])(O)=[O:35].[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:34]([OH:37])([C:11]([F:14])([F:13])[F:12])=[O:35].[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[C:7]2[C:3]([CH:4]=[N:5][NH:6]2)=[C:2]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([C:29]([OH:31])=[O:30])[CH:24]=2)[CH:10]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 177505172-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol esterHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazole

Produkt 2

HCID 6422Trifluoroacetic acidHCID 897828414-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

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 mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.302 g, 1.140 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (0.3 g, 1.140 mmol), and PdCl2(dppf) (0.042 g, 0.057 mmol) in dioxane (10 mL) was combined with aqueous saturated NaHCO3 (3 mL) to give a light brown suspension. The reaction mixture was heated in a microwave reactor at 140° C. for 45 minutes and was then cooled, filtered, concentrated in vacuo, and purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 15-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give a TFA salt of the title compound. ESI-MS m/z [M+H]+ calc'd for C14H8F3N3O2, 308.1. found 308.1.

Aufarbeitung

  1. customto give a light brown suspension
  2. temperaturewas then cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column)
  6. washeluting with a gradient of 15-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-8b092a4b92984b9087448cbb51eecf8c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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