Sodium Carbonate → 4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridine

HRID 2359109Notes

Reaction equation

HRID 2359109 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O1.[CH2:16]([N:18]1[CH:22]=[C:21](I)[C:20]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[N:19]1)[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH2:16]([N:18]1[CH:22]=[C:21]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[C:20]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[N:19]1)[CH3:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 672606401-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole

Product 1

HCID 672605734-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridineYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.60 mmol) and bis(tricyclohexylphosphine)palladium(II) chloride (0.05 mmol) were weighed into a microwave vial (reaction volume 2-5 mL). A solution of 1-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole (0.50 mmol) in 3.3 mL degassed dioxane and 1.1 mL of a degassed 2 M aqueous sodium carbonate solution were added. The reaction mixture was purged with argon, the microwave vial was capped with a septum and transferred to a laboratory microwave oven. The reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min. After cooling to room temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100) to afford 105 mg 4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridine (82% yield).

Workup

  1. additionwere added
  2. customThe reaction mixture was purged with argon
  3. customthe microwave vial was capped with a septum
  4. customtransferred to a laboratory microwave oven
  5. customThe reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min
  6. additionthe reaction mixture was diluted with water
  7. extractionextracted with dichloromethane
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100)

Sources & evidence

ORD record
ord-c361ba27f0a5435e8cf6a29d7dbca3d1
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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