Water → Methyl 6-chloro-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate

HRID 711451

Reaktionsgleichung

Reaktionsgleichung von HRID 711451
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].[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[CH3:23].CCN(CC)CC.O>C(#N)C.CCOC(C)=O>[Cl:12][C:10]1[CH:9]=[C:8]([C:13]#[N:14])[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([F:15])=[C:17]([CH3:23])[CH:18]=2)[N:11]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 679814-Fluoro-m-toluidineHCID 58317683Methyl 2,6-dichloro-4-cyanonicotinate

Produkt 1

HCID 58317541Methyl 6-chloro-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 2,6-dichloro-4-cyanonicotinate (500 mg, 2.164 mmol), 4-fluoro-3-methylaniline (325 mg, 2.60 mmol) and Et3N (0.452 mL, 3.25 mmol) in ACN (5 mL) was stirred at 50° C. for 24 h. Water and EtOAc were added to the mixture and the aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 to give the title compound, which contains some starting material and was used without further purification (390 mg). [M+H] calc'd for C15H11ClFN3O2, 320. found, 320.

Aufarbeitung

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-331a83e14590484ab21628e242de4e27
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181255B2

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