1-Benzylpiperazine → 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester

HRID 206

Reaktionsgleichung

Reaktionsgleichung von HRID 206
CCOC(=O)c1cc(=O)c2cc(OC)cc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CCOC(=O)c1cc(=O)c2cc(OC)cc(N3CCN(Cc4ccccc4)CC3)c2o1

Komponenten

7

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Tris(dibenzylideneacetone)dipalladium(0) (0.280 g, 0.31 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.457 g, 0.73 mmol), ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate (2 g, 6.11 mmol), 1-benzylpiperazine (1.169 mL, 6.73 mmol) and cesium carbonate (2.79 g, 8.56 mmol) were heated under argon to 80 °C in toluene (60 mL) overnight. The reaction mixture was allowed to cool. Ethylacetate was added and the organic mixture was filtered. The filtrate was evaporated onto Silica gel. The crude product was added to a silica gel column and was eluted with MeOH/DCM 0-5%. 1H NMR in CDCl3 is consistent with desired product MS (m+1) = 423. HPLC Peak RT = 3.38 minutes is product. Purity = 63%.

Quellen und Nachweise

ORD-Eintrag
ord-a7f71cce88db46cba0388c01927b5a88
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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