Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate → Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylate

HRID 717819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717819
[Cl:1][C:2]1[C:3]([CH2:19][NH:20][CH:21]=O)=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[C:3]2[N:4]([CH:21]=[N:20][CH:19]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Komponenten

3

Edukt 1

HCID 58515924Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate

Produkt 1

HCID 58515979Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate (2.6 g, 8.5 mmol) was stirred in phosphoryl chloride (80 mL) and heated at 90° C. for 1 hour. Evaporation and purification by flash column chromatography with ethyl acetate in hexanes (0-100%) gave the desired compound (0.60 g, 40%). LCMS calculated for C15H11ClFN2O2 (M+H)+: m/z=305.1. found: 304.9. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (s, 1H), 7.91 (s, 1H), 7.60 (m, 1H), 7.43 (m, 3H), 7.38 (m, 1H), 3.60 (s, 3H).

Aufarbeitung

  1. customEvaporation and purification by flash column chromatography with ethyl acetate in hexanes (0-100%)

Quellen und Nachweise

ORD-Eintrag
ord-fb8aeb739efa46268a11c5f7419426ee
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193721B2

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