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

HRID 2359109ノート

反応式

HRID 2359109 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c361ba27f0a5435e8cf6a29d7dbca3d1
出典データセット
uspto-grants-2014_04
特許番号
US08685974B2

反応ノート

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