Ethyl (4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetate → HCID 89782950, Verbindung

HRID 58062

Reaktionsgleichung

Reaktionsgleichung von HRID 58062
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)O1.Br[C:24]1[C:25]([CH3:36])=[N:26][N:27]([CH2:30][C:31]([O:33]CC)=[O:32])[C:28]=1[CH3:29]>O1CCOCC1.C([O-])(O)=O.[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]>[CH3:36][C:25]1[C:24]([C:9]2[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)=[C:28]([CH3:29])[N:27]([CH2:30][C:31]([OH:33])=[O:32])[N:26]=1

Komponenten

6

Edukt 2

HCID 2778421Ethyl (4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetateHCID 897828064-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole

Produkt 1

HCID 89782950HCID 89782950, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a microwave vial were added a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.3 g, 0.961 mmol), ethyl 2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetate (0.351 g, 1.346 mmol) and PdCl2(dppf) (0.035 g, 0.048 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the residue was purified by preparative HPLC, eluting with a gradient of 40-50% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes. Two products were separated. The product-containing fractions were combined and the volatiles removed in vacuo to give the title compound as the major product. ESI-MS m/z [M+H]+ calc'd for C15H13F3N4O2, 339.1. found 339.2.

Aufarbeitung

  1. additionTo a microwave vial were added
  2. concentrationThe reaction mixture was subsequently concentrated
  3. customthe residue was purified by preparative HPLC
  4. washeluting with a gradient of 40-50% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes
  5. customTwo products were separated
  6. customthe volatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d56eb2d5b1e4865a9cb133cdba80470
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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