1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone → 5-(2,4-Difluorophenyl)-3,4-dihydro-7-hydroxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

HRID 394073Notes

Reaction equation

HRID 394073 reaction equation
Br[C:2]1[CH:11]=[C:10]([O:12]C)[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:25])[N:7]2[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:15]=1.ClC1C=CC=C(Cl)C=1N1C2C(=C([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=3[F:52])C=C(O)C=2)CCC1=O>>[F:51][C:48]1[CH:47]=[C:46]([F:52])[CH:45]=[CH:50][C:49]=1[C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:25])[N:7]2[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:15]=1

Participants

3

Reactant 2

HCID 226480931-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinoneHCID 226481255-Bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone2×

Product 1

HCID 226480135-(2,4-Difluorophenyl)-3,4-dihydro-7-hydroxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

Procedure

5-(2,4-Difluorophenyl)-3,4-dihydro-7-hydroxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone was prepared from 5-bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone (INTERMEDIATE 15) by a procedure analogous to that described in INTERMEDIATE 3. Mass spectrum (ESI) 424.1 (M+1). 1H NMR (500 MHz, DMSO-d6): δ 9.44 (s, 1H); 7.96 (d, J=8.0 Hz, 1H); 7.75 (s, 1H); 7.59 (d, J=8.0 Hz, 1H); 7.41 (m, 2H); 7.18 (t, J=6.0 Hz, 2H); 6.33 (s, 1H); 5.63 (s, 1H); 3.84 (s, 3H); 2.61 (m, 4H); 2.09 (s, 3H).

Sources & evidence

ORD record
ord-c4213a25ca0f4ab9a0e2503d6eba756e
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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