Sodium Carbonate → HCID 67282750, compound

HRID 1616163Notes

Reaction equation

HRID 1616163 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=2)[N:8]=[CH:7]1.[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>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].O>[O:16]=[C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=2)[N:8]=[CH:7][N:6]1[CH2:5][C:4]1[CH:22]=[CH:23][CH:24]=[C:2]([C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734379(Pyridin-4-yl)boronic acidHCID 67282590HCID 67282590, compound

Product 1

HCID 67282750HCID 67282750, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a microwave vial was added ethyl 3-(3-bromobenzyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate (0.050 g, 0.13 mmol), pyridine-4-boronic acid (0.032 g, 0.26 mmol) in a solution of 1,4-dioxane (2 mL) and water (0.4 mL). Sodium carbonate (0.041 g, 0.39 mmol) was added followed by [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride (0.013 g, 0.015 mmol). The reaction mixture was heated at 90° C. for 16 h. The mixture was then concentrated and to the residue was added dichloromethane (3 mL) and water (1 mL). After separation, the aqueous phase was extracted with dichloromethane (3 mL). The combined organic layers were then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford ethyl 4-oxo-3-(3-(pyridin-4-yl)benzyl)-3,4-dihydroquinazoline-6-carboxylate. LC-MS: (FA) ES+ 386.

Workup

  1. concentrationThe mixture was then concentrated and to the residue
  2. additionwas added dichloromethane (3 mL) and water (1 mL)
  3. customAfter separation
  4. extractionthe aqueous phase was extracted with dichloromethane (3 mL)
  5. washThe combined organic layers were then washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-77695eb1331746c8b2d218a74fb1d6b3
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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