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Trifluoroacetic acid → Methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate

HRID 1259328
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259328
[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:4](=[O:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O.[I:30]N1C(=O)CCC1=O.[Al]>O.C(Cl)Cl>[I:30][C:7]1[N:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[C:2]=1[CH3:1]
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Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 58432791AZ-32S-methyl-ester

Produkt 1

HCID 66738777Methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (1.5 g, 4.8 mmol), dry DCM (7.0 mL), trifluoroacetic acid (3.0 mL) and N-iodosuccinimide (1.0 g, 4.5 mmol) were mixed and stirred at RT in the dark (flask covered with aluminum foil). After 5 h, water (5 mL) was added and the mixture was concentrated by rotary evaporation. Water (3 mL) was added once more and the mixture was concentrated as described above. The resulting mixture was diluted with acetonitrile to a total volume of 50 mL. Purification by preparative HPLC with acetonitrile-water as eluent (neutral eluent) gave methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.905 g, 46%) as a yellow crystalline solid.

Aufarbeitung

  1. concentrationthe mixture was concentrated by rotary evaporation
  2. additionWater (3 mL) was added once more
  3. concentrationthe mixture was concentrated
  4. additionThe resulting mixture was diluted with acetonitrile to a total volume of 50 mL
  5. customPurification by preparative HPLC with acetonitrile-water as eluent (neutral eluent)

Quellen und Nachweise

ORD-Eintrag
ord-8013738c384b4475972c89694974ab64
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466284B2

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