Potassium Carbonate → HCID 21873663, compound

HRID 2233332Notes

Reaction equation

HRID 2233332 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1.[C:13]1(/[CH:19]=[CH:20]/B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)(Cl)Cl.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>[CH:20](/[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1)=[CH:19]\[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

Product 1

HCID 21873663HCID 21873663, compoundYield 57.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (10.0 g, 44 mmole) and trans-2-phenylvinylboronic acid (9.0 g, 61 mmole) were dissolved in 1,4-dioxane (200 mL) and the solution was degassed with argon. (Ph3P)4Pd (2.5 g, 2.2 mmole) was added, followed by a solution of potassium carbonate (15 g, 109 mmole) in H2O (100 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with CHCl3 (400 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was recrystallized from hot EtOAc to afford the title compound (6.4 g, 57.5%): MS (ES) m/e 253.0 (M+H)+.

Workup

  1. customthe solution was degassed with argon
  2. temperatureThe reaction was heated
  3. temperatureat reflux under argon overnight
  4. washThe solution was washed sequentially with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe solid residue was recrystallized from hot EtOAc

Sources & evidence

ORD record
ord-807f77176e3e498ba67d6ad6d8476001
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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