N-methyl-2-pyrrolidone → 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazole

HRID 1946992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946992
[CH2:1]([S:5][C:6]1[N:11]=[C:10](Cl)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[N+:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[N:19][NH:20]2)([O-:15])=[O:14].[H-].[Na+].CN1C(=O)CCC1>O>[CH2:1]([S:5][C:6]1[N:11]=[C:10]([N:20]2[C:21]3[C:17](=[C:16]([N+:13]([O-:15])=[O:14])[CH:24]=[CH:23][CH:22]=3)[CH:18]=[N:19]2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 180574-NitroindazoleHCID 24758Sodium hydrideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidine

Produkt 1

HCID 597435151-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazoleAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a flask loaded with 2-butylsulfanyl-4-chloro-pyrimidine (202 mg) was added 4-nitro-1H-indazole (228 mg), followed by NaH (60% dispersion in mineral oil, 84 mg) and NMP (4 mL). The resulting mixture was stirred at RT overnight, water added, and the mixture extracted with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 80:20) to give 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazole (156 mg).

Aufarbeitung

  1. extractionthe mixture extracted with EtOAc
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-028e3271d016484f8c8668886a636f49
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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