Sodium Carbonate → HCID 86273586, compound

HRID 1497739Notes

Reaction equation

HRID 1497739 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])[C:5]2([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:27][C:28]1[C:32](B(O)O)=[C:31]([CH3:36])[O:30][N:29]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:27][C:28]1[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[C:5]3([CH3:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:31]([CH3:36])[O:30][N:29]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600790HCID 117600790, compound

Product 1

HCID 86273586HCID 86273586, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-Bromo-3,4-dimethyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one (140 mg, 0.42 mmol) in dioxane (10 mL) is added Na2CO3 (67 mg, 0.64 mmol) and 3,5-dimethylisoxazole-4-boronic acid (78 mg, 0.55 mmol) and Pd(dppf)Cl2 then the mixture is refluxed at 100° C. overnight. The reaction is concentrated and is purified by chromatography on silica gel to give the desired product.

Workup

  1. concentrationThe reaction is concentrated
  2. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bb99b1407bb042e5996366316bac1b84
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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