2-Bromo-3-methoxypyridine → HCID 66666788, compound

HRID 1620328Notes

Reaction equation

HRID 1620328 reaction equation
C(=O)([O-])O.[Na+].[Cl:6][C:7]1[CH:30]=[CH:29][C:10]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2B2OC(C)(C)C(C)(C)O2)=[CH:9][CH:8]=1.Br[C:32]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][N:33]=1>O1CCOCC1.O.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>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[C:32]2[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 903642-Bromo-3-methoxypyridineHCID 516892Sodium BicarbonateHCID 66667277HCID 66667277, compound

Product 1

HCID 66666788HCID 66666788, compoundYield 18.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.325 g, 0.28 mmol) and 1M aqueous solution of sodium hydrogen carbonate (5.6 mL, 5.6 mmol) were added to 4-(4-chlorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Preparation 13, 1.0 g, 2.8 mmol) and 2-bromo-3-methoxypyridine (0.528 g, 2.8 mmol) in 1,4-dioxane (30 mL). The mixture was heated at 85° C. for 18 hours under a nitrogen atmosphere, then cooled, diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The organic layer was washed with water (2×30 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford an oil. The crude product was purified by silica gel chromatography eluting with 10 to 80% tert-butyl dimethyl ether in heptane to yield the title compound as a white solid (0.175 g).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe organic layer was washed with water (2×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 10 to 80% tert-butyl dimethyl ether in heptane

Sources & evidence

ORD record
ord-540980c6c3ae407fb0f63d337d82600f
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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