Triethylamine → HCID 58266751, Verbindung

HRID 1505838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505838
[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]([NH2:15])=O)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:15])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 582667993-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amide

Produkt 1

HCID 58266751HCID 58266751, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled solution (0° C.) of a mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid amide (5.0 g, 17.2 mmol) and triethylamine (24.0 mL, 172 mmol) in THF (200 mL) was slowly added trifluoroacetic anhydride (12.0 mL, 86 mmol). Upon complete addition, the reaction mixture was allowed to warm to ambient temperature and the stirring was continued for an additional 4 h. After this time, the solvent was removed in vacuo and the resultant residue was loaded onto H-MN. The residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane) to afford the title compound as a pale brown solid (2.30 g, 49%). 1H NMR (DMSO-D6, 300 MHz): 13.05 (s, 1H), 9.08-9.04 (m, 2H), 8.91 (d, J=1.1 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H). LCMS (Method B): RT=2.98 min, M+H+=271, 273.

Aufarbeitung

  1. additionUpon complete addition
  2. customAfter this time, the solvent was removed in vacuo
  3. customThe residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-67bca9f36b48441bbc2bb89bc13b6a77
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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