(2,5-Difluorophenyl)boronic acid → 5-(2,4-Difluorophenyl)-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

HRID 394072Notes

Reaction equation

HRID 394072 reaction equation
Br[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[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.FC1C=CC(F)=CC=1B(O)O.ClC1C=CC=C(Cl)C=1N1C2C(=C([C:57]3[CH:62]=[CH:61][C:60]([F:63])=[CH:59][C:58]=3[F:64])C=C(OC)C=2)CCC1=O>>[F:63][C:60]1[CH:59]=[C:58]([F:64])[CH:57]=[CH:62][C:61]=1[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[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

4

Reactant 3

HCID 2734335(2,5-Difluorophenyl)boronic acidHCID 226480981-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinoneHCID 226481255-Bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone2×

Product 1

HCID 226481655-(2,4-Difluorophenyl)-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

Procedure

5-(2,4-Difluorophenyl)-3,4-dihydro-7-methoxy-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 14) and 2,5-difluorophenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 438.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.06 (d, J=5.0 Hz, 1H); 7.89 (s, 1H); 7.42 (d, J=5.0 Hz, 2H); 7.01 (m, 2H); 6.49 (s, 1H); 5.86 (s, 1H); 3.95 (s, 3H); 3.68 (s, 3H); 2.81 (m, 4H); 2.21 (s, 3H).

Sources & evidence

ORD record
ord-e8f5aeac41594297b68848da0f0f56d0
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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