Sodium Bicarbonate → 3-(6-(trifluoromethyl)-1H-indazol-4-yl)benzenesulfonamide

HRID 58098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58098
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.[S:15]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:18])(=[O:17])[NH2:16].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].O1CCOCC1>[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:24]=[C:19]([S:15]([NH2:16])(=[O:18])=[O:17])[CH:20]=[CH:21][CH:22]=2)[CH:10]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 441193233-(Aminosulphonyl)benzeneboronic acid

Produkt 1

HCID 897830113-(6-(trifluoromethyl)-1H-indazol-4-yl)benzenesulfonamideAusbeute 69,5 %

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

4-Bromo-6-(trifluoromethyl)-1H-indazole (40 mg, 0.151 mmol), (3-sulfamoylphenyl)boronic acid (45.5 mg, 0.226 mmol), PdCl2(dppf) (11.04 mg, 0.015 mmol), sodium bicarbonate (323 μL, 0.604 mmol), and dioxane were mixed in a 10 mL vial to give an orange suspension. The vial was sealed and then heated to 140° C. for 20 minutes in a microwave reactor. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3). The pure fractions were lyophilized to give the title compound as a white solid (35.8 mg, 69.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.50 (s, 2H), 7.53 (s, 1H), 7.75-7.80 (m, 1H), 7.92-7.94 (m, 1H), 8.02 (s, 1H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1H), 8.40 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H10F3N3O2S, 342.0. found 342.2.

Aufarbeitung

  1. customto give an orange suspension
  2. customThe vial was sealed
  3. filtrationThe reaction mixture was subsequently filtered
  4. customthe product was purified by preparative HPLC
  5. washeluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3)

Quellen und Nachweise

ORD-Eintrag
ord-367f38fb34bc4b4e8d6789a8dc992bd1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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