N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Methyl 1-cyclopropyl-9-methyl-8-(4-(methylamino)-phenyl)-4-oxo-4H-quinolizine-3-carboxylate

HRID 1854840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854840
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=1>>[CH:13]1([C:9]2[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6](=[O:20])[N:5]3[C:10]=2[C:11]([CH3:12])=[C:2]([C:26]2[CH:27]=[CH:28][C:23]([NH:22][CH3:21])=[CH:24][CH:25]=2)[CH:3]=[CH:4]3)[CH2:15][CH2:14]1

Komponenten

3

Edukt 2

HCID 11957892N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Produkt 1

HCID 86696558Methyl 1-cyclopropyl-9-methyl-8-(4-(methylamino)-phenyl)-4-oxo-4H-quinolizine-3-carboxylateAusbeute 89,4 %

Versuchsvorschrift

Methyl 1-cyclopropyl-9-methyl-8-(4-(methylamino)-phenyl)-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (74 mg, 0.25 mmol) and N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline (71 mg, 0.31 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6) afforded the title compound as a yellow solid (81 mg, 81%). ESI-MS m/z: 363 (M+H)+.

Aufarbeitung

  1. customMethyl 1-cyclopropyl-9-methyl-8-(4-(methylamino)-phenyl)-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6)

Quellen und Nachweise

ORD-Eintrag
ord-1f3bf5b5dff7442bb6b2b3fc9b58a6ff
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962842B2

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