Triethylamine → methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

HRID 20650

Reaktionsgleichung

[C]=O.Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:30])[C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:29])[CH:12]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C.CO>[Cl:30][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:29])[CH:12]=1)[C:13]([O:14][CH3:15])=[O:29]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Carbon monoxide was bubbled through a mixture of 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.240 g, 0.514 mmol, Example 11), Pd(OAc)2 (11 mg, 0.051 mmol), DPPP (21 mg, 0.051 mmol), triethylamine (0.22 mL, 1.5 mmol), methanol (1 mL), and anhydrous DMF (4 mL). The reaction was heated at 80° C. for 2 d under an atmosphere of CO and then allowed to cool to rt. The mixture was filtered though Celite, washed with EtOAc, and concentrated to give methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate.

Aufarbeitung

temperatureto cool to rt
filtrationThe mixture was filtered though Celite
washwashed with EtOAc
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-fdf8967d91d349038d721fcbf25a7dc0
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745646B2

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