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Ethanol → 2-(Benzofuran-2-carbonylamino)-4-(8-methyl-5-quinolyl)thiophene-3-carboxylic acid

HRID 387501
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387501
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[C:17]=1[C:18]([O:20]C(C)(C)C)=[O:19])=[O:11].[CH3:33][C:34]1[CH:35]=[CH:36][C:37](B(O)O)=[C:38]2[C:43]=1[N:42]=[CH:41][CH:40]=[CH:39]2.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:37]2[CH:36]=[CH:35][C:34]([CH3:33])=[C:43]3[C:38]=2[CH:39]=[CH:40][CH:41]=[N:42]3)[C:17]=1[C:18]([OH:20])=[O:19])=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 4715077(8-Methylquinolin-5-yl)boronic acidHCID 59225740Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

Produkt 1

HCID 461866592-(Benzofuran-2-carbonylamino)-4-(8-methyl-5-quinolyl)thiophene-3-carboxylic acidAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (7), (8-methyl-5-quinolyl)boronic acid (48), Tetrakis(triphenylphosphine)palladium(0), and sodium carbonate, were combined in 2:1:1 ethanol, toluene and water the biphasic mixture was stirred vigorously in sealed vial at 70° C. After 2 hours, the mixture was filtered through Celite and the Celite rinsed with methylene chloride. The organic fraction of the filtrate was washed with water, dried with sodium sulfate, filtered, concentrated, triturated in methanol, centrifuged, decanted and the resulting solid was dried under vacuum and treated with a 1:1 mixture of methylene chloride and trifluoroacetic acid. After 4 hours the mixture was concentrated in vacuo, and the residue triturated in methylene chloride, centrifuged, decanted and dried under high vacuum to give 49A as a white powder (18.1 mg, 31%). 1H NMR (500 MHz, DMSO d6) δ=12.93 (br, 1H), 12.60 (s, 1H), 8.94 (m, 1H), 8.01 (d, 1H), 7.89 (s, 1H), 7.87 (d, 1H), 7.75 (d, 1H), 7.66 (d, 1H), 7.57 (t, 1H), 7.54 (dd, 1H), 7.44-7.41 (m, 3H), 7.11 (s, 1H), 2.76 (s, 3H) ppm. ESI MS [M+H] 429.22.

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. washthe Celite rinsed with methylene chloride
  3. washThe organic fraction of the filtrate was washed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customtriturated in methanol
  8. customdecanted
  9. customthe resulting solid was dried under vacuum
  10. additiontreated with a 1:1 mixture of methylene chloride and trifluoroacetic acid
  11. concentrationAfter 4 hours the mixture was concentrated in vacuo
  12. customthe residue triturated in methylene chloride
  13. customdecanted
  14. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c564ec5730ad43a3a7592234191e4dec
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372991B2

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