Sodium Carbonate → HCID 58994242, compound

HRID 12736Notes

Reaction equation

HRID 12736 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.[F:14][C:15]1[C:20](I)=[CH:19][CH:18]=[C:17]([CH3:22])[N:16]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:14][C:15]1[C:20]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[CH:19][CH:18]=[C:17]([CH3:22])[N:16]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 248204942-Fluoro-3-iodo-6-methylpyridine

Product 1

HCID 58994242HCID 58994242, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-pyrimidine-5-boronic acid (1.16 g, 6.32 mmol) was dissolved in degassed n-PrOH (22 ml) and then 2-fluoro-6-methyl-3-iodopyridine (870 mg, 3.67 mmol), Na2CO3 (778 mg, 7.34 mmol), PPh3 (96 mg, 0.37 mmol) and Pd(OAc)2 (41 mg added in three portions) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 691 mg of the title compound (75% yield).

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPrOH

Sources & evidence

ORD record
ord-77619ad5c1b3442e89739e7524874589
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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