N-(3-Methoxycarbonyl-6-methylphenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide → 5-Bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

HRID 394071Notes

Reaction equation

HRID 394071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:26])[CH2:14][CH2:15][C:16]2[C:21](Br)=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=2[Br:25])[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:4].BrC1C=C(OC)C=C2C=1CCC(=O)N2C1C(Cl)=CC=CC=1Cl>>[Br:25][C:17]1[CH:18]=[C:19]([O:23][CH3:24])[CH:20]=[C:21]2[C:16]=1[CH2:15][CH2:14][C:13](=[O:26])[N:12]2[C:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=1

Participants

3

Reactant 2

HCID 22647874N-(3-Methoxycarbonyl-6-methylphenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamideHCID 226479975-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Product 1

HCID 226481255-Bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone

Procedure

5-Bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone was prepared from N-(3-methoxycarbonyl-6-methylphenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide by a procedure analogous to that described in INTERMEDIATE 1, Step E. Mass spectrum (ESI) 374.0 (M-OMe). 1H NMR (500 MHz, CDCl3): δ 8.02 (dd, J=2.0, 8.0 Hz, 1H); 7.80 (d, J=8.5 Hz, 1H); 6.80 (d, J=2.5 Hz, 1H); 5.73 (d, J=2.5 Hz, 1H); 3.89 (s, 3H); 3.63 (s, 3H); 3.16 (m, 2H); 2.80 (m, 2H); 2.13 (s, 3H).

Sources & evidence

ORD record
ord-0b30f72c17af4c4595292070ea961403
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…