Methyl 3-azido-6'-methoxy-6-(4-methoxyphenyl)-2,3'-bipyridine-4-carboxylate → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

HRID 2410687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410687
[N:1]([C:4]1[C:5]([C:22]2[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[CH3:29][O:28][C:25]1[N:24]=[C:23]2[NH:1][C:4]3[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)=[N:6][C:5]=3[C:22]2=[CH:27][CH:26]=1

Komponenten

3

Edukt 1

HCID 86663008Methyl 3-azido-6'-methoxy-6-(4-methoxyphenyl)-2,3'-bipyridine-4-carboxylate

Produkt 1

HCID 66605458methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

A solution of methyl 3-azido-6′-methoxy-6-(4-methoxyphenyl)-2,3′-bipyridine-4-carboxylate (120 mg, 0.31 mmol) in 1,2-dichlorobenzene (4 mL) was heated at 180° C. for 10 min with gas evolution. The solvent was removed under vacuum and the product was purified by silica gel radial chromatography (step gradient elution with hexane containing 50 to 100% methylene chloride). This gave methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (80 mg, 72% yield) as a yellow solid. MS (ESI) m/z 364.1 (M+H). 1H NMR (CDCl3) δ ppm 9.61 (1H, s), 8.49 (1H, d, J=8.55 Hz), 8.14 (1H, s), 8.07 (2H, d, J=8.85 Hz), 7.02 (2H, d, J=8.85 Hz), 6.73 (1H, d, J=8.55 Hz), 4.06 (3H, s), 4.04 (3H, s), 3.87 (3H, s).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe product was purified by silica gel radial chromatography (step gradient elution with hexane containing 50 to 100% methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-5306b336de7f4f7693afe7cde550d96f
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815840B2

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