(4-Fluoro-2-methylphenyl)boronic acid → 3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone

HRID 394069Notes

Reaction equation

HRID 394069 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]2C1C(Cl)=CC=CC=1Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[C:26]([CH3:33])[CH:25]=1.ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C(OC)C=2)CCC1=O>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][C:6](=[O:22])[NH:7]3)=[C:26]([CH3:33])[CH:25]=1

Participants

4

Reactant 3

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 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)-quinolinone

Product 1

HCID 867595473,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone

Procedure

1-2,6-Dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-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 4-fluoro-2-methylphenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 430.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.50 (m, 2H); 7.36 (m, 1H); 7.17 (m, 1H); 6.98 (m, 2H); 6.45 (s, 1H); 5.89 (s, 1H); 3.69 (s, 3H); 2.72 (m, 4H); 2.15 (s, 3H).

Sources & evidence

ORD record
ord-7e49b8308130482dac27cb58d7bb0870
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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