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

HRID 1361647Notes

Reaction equation

HRID 1361647 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+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.O1CCOCC1>[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

10

Reactant 5

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 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 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

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 C1lH9ClN2O: 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-9354e217929e412bb8358f067b529530
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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