Pyrazole → [3-(1H-Pyrazol-1-yl)phenyl]acetic acid

HRID 15784

反応式

HRID 15784 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[C@@H]1(N)CCCC[C@H]1N.CCCCCCCCCCCC.Br[C:33]1[CH:34]=[C:35]([CH2:39][C:40]([OH:42])=[O:41])[CH:36]=[CH:37][CH:38]=1.[OH-].[Na+]>O1CCOCC1.[Cu]I>[N:1]1([C:33]2[CH:34]=[C:35]([CH2:39][C:40]([OH:42])=[O:41])[CH:36]=[CH:37][CH:38]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

参加物

9

反応物 6

HCID 1048PyrazoleHCID 8182DodecaneHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 438061,2-Diaminocyclohexane, trans-HCID 74653(3-Bromophenyl)acetic acid

生成物 1

HCID 21062671[3-(1H-Pyrazol-1-yl)phenyl]acetic acid収率 65%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

実験手順

Pyrazole (1.2 eq), Cs2CO3 (2.5 eq), CuI (0.5 eq), trans-1,2-cyclohexanediamine (0.6 eq) and dodecane (1 eq), were added to a stirred solution of 3-bromophenylacetic acid (1 eq) in dioxane at room temperature under an inert atmosphere. The mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min), then added to a 1N aqueous solution of NaOH, and extracted with Et2O. The aqueous phase was acidified to pH=3 with HCl 2N, then extracted with ethyl acetate; this phase was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) eluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1, affording the title compound in 65% yield.

後処理

  1. customThe mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min)
  2. extractionextracted with Et2O
  3. extractionextracted with ethyl acetate
  4. washthis phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified on SPE cartridge (Silica)
  8. washeluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1

出典と根拠

ORDレコード
ord-0a2d14e5ae3c4320bcb0991c6c6eb791
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

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