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

HRID 394055Notes

Reaction equation

HRID 394055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:23])[CH2:11][CH2:12][C:13]1[C:18](Br)=[CH:17][C:16]([O:20][CH3:21])=[CH:15][C:14]=1[Br:22].C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1.[Cu]I>[Br:22][C:14]1[CH:15]=[C:16]([O:20][CH3:21])[CH:17]=[C:18]2[C:13]=1[CH2:12][CH2:11][C:10](=[O:23])[N:9]2[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22647977N-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide

Product 1

HCID 226479975-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of 340 mg of N-(2,6-dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide in 20 mL of pyridine was added CuI (137 mg) and powdered, dried K2CO3 (99 mg). The resulting mixture was heated to 160° C. in a sealed tube overnight (20 h), then concentrated. The reside was purified by flash chromatography on a Biotage 40S column, eluting with 100% CH2Cl2, to yield 5-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone as a white solid. Mass spectrum (ESI) 402.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.48 (d, J=8.0 Hz, 2H); 7.34 (t, J=8.0 Hz, 1H); 6.83 (d, J=2.5 Hz, 1H); 5.77 (d, J=2.5 Hz, 1H); 3.67 (s, 3H); 3.18 (m, 2H); 2.84 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe reside was purified by flash chromatography on a Biotage 40S column
  3. washeluting with 100% CH2Cl2

Sources & evidence

ORD record
ord-c46e5bb3780643329dfaed9cb4e27d29
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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