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

HRID 15784

반응식

HRID 15784 반응식
[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

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a2d14e5ae3c4320bcb0991c6c6eb791
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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