Sodium Bicarbonate → HCID 89783243, Verbindung

HRID 58070

Reaktionsgleichung

Reaktionsgleichung von HRID 58070
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:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH2:25][C:26](=[O:32])[NH:27]3)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:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH2:25][C:26](=[O:32])[NH:27]3)[CH:10]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 467392234-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

Produkt 2

HCID 6422Trifluoroacetic acidHCID 89783243HCID 89783243, VerbindungAusbeute 46 %

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 (0.026 g, 0.096 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (0.025 g, 0.096 mmol) and PdCl2(dppf) (3.53 mg, 4.82 μmol) in dioxane (4 mL) and aqueous saturated NaHCO3 (3 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 30% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 10 minutes. The product-containing fractions were combined and volatiles evaporated in vacuo to give a TFA salt of the title compound as a light brown solid (0.014 g, 0.044 mmol, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.50 (s, 2H), 6.94 (d, J=7.58 Hz, 1H), 7.17 (dd, J=7.96, 0.88 Hz, 1H), 7.29-7.44 (m, 1H), 7.46-7.53 (m, 1H), 7.94 (s, 1H), 8.15 (s, 1H), 10.55 (s, 1H), 13.70 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C16H10F3N3O, 318.1. found 318.15.

Aufarbeitung

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customthe crude residue was purified by preparative HPLC
  3. washeluting with 30% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 10 minutes
  4. customvolatiles evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0301b4b3e0ca4e41a1f2c073b48dc6a4
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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