5-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone → 5-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

HRID 394067Notes

Reaction equation

HRID 394067 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:22])[N:7]2[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1B(O)O.ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C(OC)C=2)CCC1=O>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=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:22])[N:7]2[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21]

Participants

4

Reactant 3

HCID 226479975-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×HCID 226480981-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinoneHCID 226481162-Chloro-5-fluorobenzeneboronic acid

Product 1

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

Procedure

5-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone was prepared from 5-bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 1) and 2chloro-5-fluorophenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 450.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.52 (dd, J=3.0 Hz, 8.0 Hz, 2H); 7.25-7.42 (m, 3H); 7.10 (dt, J=2.5 Hz, 1H); 6.47 (d. J=2.0 Hz, 1H); 5.91 (d, J=2.5 Hz, 1H); 3.70 (s, 3H), 2.62-2.89 (m 4H).

Sources & evidence

ORD record
ord-bb9d403023be4533b2c04b7a522c3cb4
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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