Sodium Carbonate → HCID 57445395, compound

HRID 1993356Notes

Reaction equation

HRID 1993356 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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].C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([F:9])[CH:11]=2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 57445395HCID 57445395, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-bromo-2-iodopyrimidine (3.0 g, 10 mmol) and 3-fluoro-4-methoxyphenylboronic acid (2.0 g, 12 mmol) in dioxane (15 mL) and H2O (5 mL) was added Pd(dppf)Cl2—CH2Cl2 (0.1 g, 0.12 mmol) and Na2CO3 (2.0 g, 19 mmol) under argon. The mixture was stirred at RT for 20 h and was further heated at 80° C. for 20 h. The mixture was cooled to RT and was extracted with EtOAc. The organic layer was washed with H2O, NH4Cl (sat), dried (Na2SO4), and concentrated. The crude residue was partitioned in 1:1 ether-CH2Cl2 and filtered to provide the title compound as a flake. The filtrate was concentrated and was triturated with MeOH to provide a second batch of product solid. MS (ESI pos. ion) m/z: 283, 285. Calc'd for C11H8BrFN2O: 281.98.

Workup

  1. temperaturewas further heated at 80° C. for 20 h
  2. temperatureThe mixture was cooled to RT
  3. extractionwas extracted with EtOAc
  4. washThe organic layer was washed with H2O, NH4Cl (sat)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude residue was partitioned in 1:1 ether-CH2Cl2
  8. filtrationfiltered

Sources & evidence

ORD record
ord-de62511fc952424e8516a98bb84a5166
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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