Water → Methyl 2-(1H-indazol-6-ylamino)-6-chloro-4-cyanonicotinate

HRID 2092750

Reaktionsgleichung

Reaktionsgleichung von HRID 2092750
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=2)[CH:17]=[N:16]1.CCN(CC)CC.O>C1COCC1.CCOC(C)=O>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:2]3[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([C:13]#[N:14])[C:3]=3[C:4]([O:6][CH3:7])=[O:5])[CH:22]=2)[CH:17]=[N:16]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 814231H-Indazol-6-amineHCID 58317683Methyl 2,6-dichloro-4-cyanonicotinate

Produkt 1

HCID 58317650Methyl 2-(1H-indazol-6-ylamino)-6-chloro-4-cyanonicotinateAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of methyl 2,6-dichloro-4-cyanonicotinate (250 mg, 1.082 mmol), 1H-indazol-6-amine (173 mg, 1.299 mmol) and Et3N (0.226 mL, 1.623 mmol) in THF (10 mL) was stirred at 80° C. overnight. Water and EtOAc were added to the mixture. The organic phase was washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2(Hexane/EtOAc=5/1) to give the title compound as a yellow solid (120 mg, 38.5%).

Aufarbeitung

  1. washThe organic phase was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by chromatography on SiO2(Hexane/EtOAc=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-55fcaf87709e40f2b4efbd4f4882cff3
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440689B2

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