Methanol → Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

HRID 455297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455297
C(N(CC)CC)C.[Br:8][C:9]1[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[C:16]([OH:23])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25].CO>C(Cl)(Cl)Cl.O>[Br:8][C:9]1[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[C:16]([O:23][S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2

Komponenten

7

Edukt 4

HCID 887Methanol2×HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Produkt 1

HCID 11339571Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Triethyl amine (15.9 mmol) was added to a suspension of methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (10.6 mmol) in chloroform (22 ml) over 5 min. at 20-50° C. Tosyl chloride (12.7 mmol) was added over 5 min maintaining the temperature at 40° C. for 2 h. The mixture was cooled to 20° C. over 15 min. MeOH was added over 30 min, then a mixture of MeOH:water was added over 30 min. The resulting off-white crystalline solid was collected by filtration and dried to give the target compound in 50% yield.

Aufarbeitung

  1. temperatureThe mixture was cooled to 20° C. over 15 min
  2. filtrationThe resulting off-white crystalline solid was collected by filtration
  3. customdried
  4. customto give the target compound in 50% yield

Quellen und Nachweise

ORD-Eintrag
ord-ca8124b5b495487388343032ba047f80
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497270B2

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