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Triethylamine → HCID 17864581, Verbindung

HRID 1592948
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1592948
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[N+:29]([O-:31])=[O:30]>O.CO>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[N+:29]([O-:31])=[O:30]
KomponentenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 17864580(7-Bromo-6-nitro-4-quinazolinyl)-(3-chloro-4-fluorophenyl)amine hydrochloride

Produkt 1

HCID 17864581HCID 17864581, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution (9 mL) of (7-bromo-6-nitro-4-quinazolinyl)-(3-chloro-4-fluorophenyl)amine (3.0 g, 7.55 mmol) obtained by a treatment, with triethylamine in water-methanol, of (7-bromo-6-nitro-4-quinazolinyl)-(3-chloro-4-fluorophenyl)amine hydrochloride produced according to the method described in Synthetic Example 4, acetylene 4ab (1.76 g, 9.06 mmol) synthesized according to the method of Synthetic Example 1 and triethylamine (60 mL) in DMF solution was subjected 3 times to the step of degassing under reduced pressure and displacement with nitrogen. Triphenylphosphine (118 mg, 0.46 mmol) and palladium (II) acetate (51 mg, 0.23 mmol) were added. The mixture was stirred at 80° C. for 3 hrs and allowed to cool to room temperature. The solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with water (×3) and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a nitro compound 3ab.

Quellen und Nachweise

ORD-Eintrag
ord-e11f75d9f4244918807d9786892205c2
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07294629B2

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