Sodium triacetoxyborohydride → 1-(2,6-dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone

HRID 394224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394224
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1C1C=C(O)C=C2C=1CCC(=O)N2C1C(Cl)=CC=CC=1Cl.ClC1C=CC(F)=CC=1[C:37]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[C:43]2[C:38]=1[CH2:39][CH2:40][C:41](=[O:57])[N:42]2[C:49]1[C:54]([Cl:55])=[CH:53][CH:52]=[CH:51][C:50]=1[Cl:56].[BH-](OC(C)=O)(OC(C)=O)O[C:60](C)=O.[Na+]>>[Cl:55][C:54]1[CH:53]=[CH:52][CH:51]=[C:50]([Cl:56])[C:49]=1[N:42]1[C:43]2[C:38](=[C:37]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[CH3:60])[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=2)[CH2:39][CH2:40][C:41]1=[O:57]

Komponenten

4

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 226480315-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinoneHCID 226480755-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Produkt 1

HCID 226479211-(2,6-dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone

Versuchsvorschrift

Compound 9 (COMPOUND DMM-1) was converted to aldehyde 10 via standard Swern reaction. Aldehyde 10 was coupled with amine 11 via NaB(OAc)3H to afford 12. Treatment of 12 with TFA afford 13 (EXAMPLE DMM1). Mass spectrum (ESI) for 13, 573 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-50cd2feabe4940a38b58c25951585f48
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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