Hydrochloric Acid → 3-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 2205111

Reaktionsgleichung

Reaktionsgleichung von HRID 2205111
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[C:30](B(O)O)[C:25]=2[O:24][CH2:23]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:2]3[C:3]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:4][C:5]4[C:10]([N:11]=3)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=4)=[CH:30][C:25]=2[O:24][CH2:23]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 41926592,3-Methylenedioxyphenyl boronic acidHCID 86667202HCID 86667202, Verbindung

Produkt 1

HCID 867181103-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acidAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

A suspension of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (80 mg, 0.23 mmol, 1.00 equiv), benzo[d][1,3]dioxol-4-ylboronic acid (59 mg, 0.36 mmol, 1.50 equiv), tricyclohexylphosphine (9 mg, 0.03 mmol, 0.14 equiv), Pd2(dba)3 (13 mg, 0.01 mmol, 0.06 equiv), and K3PO4 (149 mg, 0.80 mmol, 3.00 equiv). in dioxane/H2O (1/0.5 mL) in a 10-mL sealed tube was allowed to react, with stifling, overnight at 95° C. The pH value of the solution was adjusted to 7 with HCl (1N). Purification via silica gel column (dichloromethane:methanol (1:10)) afforded 35 mg (40%) of 3-(benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Aufarbeitung

  1. customto react
  2. customovernight
  3. customat 95° C
  4. customPurification via silica gel column (dichloromethane:methanol (1:10))

Quellen und Nachweise

ORD-Eintrag
ord-320bf4d8c83d42f4b42d168b923f589e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370522B2

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