Sodium Carbonate → HCID 86273346, compound

HRID 1497717Notes

Reaction equation

HRID 1497717 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.[CH3:21][C:22]1[C:26](B(O)O)=[C:25]([CH3:30])[O:24][N:23]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd]Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:26]4[C:22]([CH3:21])=[N:23][O:24][C:25]=4[CH3:30])[CH:3]=3)[NH:8][C:7](=[O:12])[N:6]2[CH3:13])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600736HCID 117600736, compound

Product 1

HCID 86273346HCID 86273346, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-Bromo-4-(4-chloro-phenyl)-3-methyl-3,4-dihydro-1H-quinazolin-2-one (0.2 g, 0.57 mmol) dissolved in dioxane (50 mL) is added 3,5-dimethylisoxazole-4-boronic acid (0.1 g, 0.74 mmol), PdCl2 (0.048 g, 0.057 mmol) and Na2CO3 aq. The mixture is stirred at 120° C. to reflux for 5 hours. Then cooled to RT, concentrated and purified by column chromatography on silica gel to give the desired compound.

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureThen cooled to RT
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-42a454e8e7c54ffc9fdf1ec15cc23715
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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