Ytterbium triflate → Methyl 6-chloro-4-(3-chlorophenyl)-2-cyclopropylquinoline-3-carboxylate

HRID 1497042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497042
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=O.[CH:18]1([C:21](=O)[CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:19]1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[CH3:26][O:25][C:23]([C:22]1[C:21]([CH:18]2[CH2:20][CH2:19]2)=[N:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:24]

Komponenten

5

Edukt 3

HCID 2733225Ytterbium triflateHCID 5231029(2-Amino-5-chlorophenyl)(3-chlorophenyl)methanoneHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Produkt 1

HCID 86682924Methyl 6-chloro-4-(3-chlorophenyl)-2-cyclopropylquinoline-3-carboxylateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of (2-amino-5-chlorophenyl)(3-chlorophenyl) methanone (81 mg, 0.31 mmol, 1 eq) and methyl 3-cyclopropyl-3-oxopropanoate (56.2 mg, 0.40 mmol, 1.3 eq) in ethanol (3 ml) was added ytterbium triflate (19 mg, 0.03 mmol, 0.1 eq) and the yellow solution was stirred overnight at room temperature. The resultant precipitate was filtered and washed with a small amount of ethanol to give the desired product (49 mg, 43%) as a white solid which did not require any further purification. MS (ESI): 372.1 (M+H)+.

Aufarbeitung

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with a small amount of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-83dd73c5ebe94ae48768693d2a42eee5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199938B2

Notizen zur Reaktion

Wird geladen…