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Sodium Carbonate → N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide

HRID 2359110
ノート
印刷プレビュー

反応式

HRID 2359110 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH:10]=2)O1.[CH2:21]([N:23]1[CH:27]=[C:26](I)[C:25]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[N:24]1)[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH2:21]([N:23]1[CH:27]=[C:26]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH:10]=2)[C:25]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[N:24]1)[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 497605002-Propionamidopyridine-4-Boronic Acid Pinacol EsterHCID 672606401-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole

生成物 1

HCID 67260817N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide収率 93.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanamide (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 152 mg N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide (93% 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-f1671475fdf04f96bfaecd27f7d54da3
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685974B2

反応ノート

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