Sodium Carbonate → 2-Chloro-3-(2-methoxypyridin-4-yl)pyridine

HRID 446298Notes

Reaction equation

HRID 446298 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[Cl:10][C:11]1[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Cl:10][C:11]1[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 150197954-Iodo-2-methoxypyridine

Product 1

HCID 583966532-Chloro-3-(2-methoxypyridin-4-yl)pyridine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 4-iodo-2-methoxypyridine (834 mg, 3.55 mmol), 2-chloropyridine-3-boronic acid (838 mg, 5.32 mmol), Na2CO3 (1.13 g, 10.7 mmol), Pd(OAc)2 (40 mg, 0.18 mmol) and P(tBu)3·HBF4 (104 mg, 0.36 mmol) was added dioxane (12 mL) and water (4 mL). The mixture was heated overnight at 100° C. in a sealed tube. The resulting mixture was diluted with EtOAc and extracted with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting solid was triturated with MeOH and dried to yield the title compound. MS m/z=221 [M+1]+. Calc'd for C21H9ClN2O: 220.66.

Workup

  1. extractionextracted with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with MeOH
  6. customdried

Sources & evidence

ORD record
ord-ae229435b2774e6cb4e5f711500353fb
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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