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

HRID 394063Notes

Reaction equation

HRID 394063 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][CH:27]=[CH:26][C:25]=1B(O)O.ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C([O:51]C)C=2)CCC1=O>>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:2]1[CH2:11][C:10]([OH:51])([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 27343222-Chlorophenylboronic 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 699198965-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-7-methoxy-2(1H)-quinolinone

Procedure

5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-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 2-chlorophenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 434.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.43-7.54 (m, 2H); 7.30-7.42 (m, 4H) 6.48 (d, J=2.5 Hz, 1H); 5.82 (d, J=2.5 Hz, 1H); 5.89 (d, J=2.5 Hz, 1H); 3.69 (s, 3H); 2.63-2.88 (m, 4H).

Sources & evidence

ORD record
ord-f720444e18e34262812554c867f04370
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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