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Pyridine → ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylate

HRID 987504
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 987504
B(O)O.[CH3:4][C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][N:6]=1.N1C=CC=CC=1.CC1N([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:37][CH3:38])[CH:33]=3)[CH:28]=2)N=C(C(OCC)=O)C=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:4][C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:37][CH3:38])[CH:33]=3)[CH:28]=2)[N:6]=1
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Komponenten

7

Edukt 4

HCID 1049PyridineHCID 61668Boronic AcidHCID 22728899ethyl 5-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-3-carboxylateHCID 178469061HCID 178469061, Verbindung

Produkt 1

HCID 22728868ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysator
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the above-prepared boronic acid (0.84 g, 3.2 mmol) and ethyl 3-methylpyrazole-5-carboxylate (0.49 g, 3.2 mmol) in 20 mL dry DCM were added pyridine (0.77 mL, 9.5 mmol) and anhydrous powder of copper(II) acetate (1.15 g, 6.3 mmol). Some activated molecular sieve powder was added afterwards. The resulting slurry was stirred for 4 days under argon. The mixture was diluted with DCM. It was filtered through celite. The blue filtrate was washed with water (×2), dried, concentrated and purified by flash column to separately afford ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylate [37% yield. Rf 0.80 (1:1 EtOAc:hexane). ES-MS: (M+H)+311] and ethyl 5-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-3-carboxylate [25% yield. Rf 0.69 (1:1 EtOAc:hexane). ES-MS: (M+H)+311]in a 1.5:1 ratio.

Aufarbeitung

  1. additionSome activated molecular sieve powder was added afterwards
  2. filtrationIt was filtered through celite
  3. washThe blue filtrate was washed with water (×2)
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-71e42d9500d4421b9837bee9dae375c4
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06632815B2

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