Sodium Carbonate → HCID 22648169, compound

HRID 394079Notes

Reaction equation

HRID 394079 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14](Br)[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:22].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[Cl:23])[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:22]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 22647916HCID 22647916, compound2×

Product 1

HCID 22648169HCID 22648169, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Palladium tetrakis triphenylphosine (140 mg, 0.12 mmol) was added to 1-(2,6-dichlorophenyl)-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (1.02 g, 2.54 mmol) (INTERMEDIATE 23), 2-chlorophenyl boronic acid (642 mg, 4.11 mmol) and sodium carbonate (436 mg, 4.11 mmol) in 150 mL toluene, 40 mL EtOH and 40 mL water under an argon atmosphere. After refluxing 3 h the solution was cooled to RT and partition between water and EtOAc. The organic phase was washed with water′(1×) and brine (1×) and dried over MgSO4. The solution was filtered and concentrated. The residue was absorbed on SiO2 and purified by silica gel bromatography using 3 to 5% acetone in DCM to give 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinazolinone as a white solid. 1H NMR(CDCl3, 500 MHz): δ 3.68 (s, 3H), 4.17 (d, 1H, J=14.0 Hz), 4.36 (d, 1H, J=14.0 Hz), 5.28 (s, 1H), 5.74 (d, 1H, J=2.3 Hz), 6.43 (d, 1H, J=2.5 Hz), 7.29-7.37 (m, 4H), 7.47-7.51 (m, 3H). MS(ES) 433 (M+H); LC 1: 3.12 min.

Workup

  1. temperatureAfter refluxing 3 h the solution
  2. custompartition between water and EtOAc
  3. washThe organic phase was washed with water′(1×) and brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customThe residue was absorbed on SiO2
  8. custompurified by silica gel bromatography

Sources & evidence

ORD record
ord-b5ea69a34654446ba99ce63b3b0a0291
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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