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

HRID 394074Notes

Reaction equation

HRID 394074 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.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C(OC)C=2)CCC1=O>>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=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 27343222-Chlorophenylboronic 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 226480575-(2-Chlorophenyl)-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

Procedure

5-(2-Chlorophenyl)-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 16) and 2-chlorophenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 436.3 (M+1). 1H NMR (500 MHz, CDCl3): 7.95 (m, 1H); 7.81 (d, J=19.0 Hz, 1H); 7.41 (m, 1H); 7.37 (d, J=8.0 Hz, 1H); 7.27 (m, 2H); 7.21 (m, 1H); 6.35 (s, 1H); 5.76 (s, 1H); 3.81 (s, 3H); 3.55 (s, 3H); 2.65 (m, 4H); 2.11 (d, J=11.5 Hz, 3H).

Sources & evidence

ORD record
ord-c8c914f312ed4ee1a49d85d2f5226d4b
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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