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

HRID 394224Notes

Reaction equation

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]

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 22648031HCID 22648031, compound

HCID 226480755-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Product 1

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

Procedure

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).

Sources & evidence

ORD record: ord-50cd2feabe4940a38b58c25951585f48
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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