Potassium Carbonate → 2-phenyl-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine

HRID 2361754노트

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HRID 2361754 반응식
Cl.Cl[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][NH2:11])=[CH:5][CH:4]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:12]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)=[CH:4][CH:5]=2)[CH2:10][NH2:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 177498342-(4-Chlorophenyl)-2-phenylethan-1-amine--hydrogen chloride (1/1)

생성물 1

HCID 111963222-phenyl-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine수율 10.6%

시약·촉매·용매 4

HCID 178418851HCID 178418851, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

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온도
135 °C

실험 절차

To a suspension of 2-(4-chlorophenyl)-2-phenylethylamine hydrochloride (134 mg, 0.5 mmol, 1.0 equiv.) (Array PPA-Q02-1) in toluene (0.8 ml) was added bis(tri-t-butylphosphine)palladium (0) (3 mg, 1 mol %) (Strem) and the mixture was purged with nitrogen. A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (107 mg, 0.55 mmol, 1:1 equiv.) (Aldrich 52, 505-7) in ethanol (0.8 ml) was added followed by potassium carbonate (415 mg, 3.0 mmol, 6 equiv.) in water (2.5 ml). The mixture was purged with nitrogen and sealed. The reaction mixture was heated in a CEM Explorer™ microwave to 135° C. for 15 minutes using 50 watts power. The solvents were removed and the residue was partitioned between ethyl acetate and 2N NaOH. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography (SiO2), eluting with a mixture of dichloromethane (90 ml):methanol (18 ml):acetic acid (3 ml):H2O (2 ml) to afford the title compound 14 mg (9%); LCMS (PS-A) Rt 1.79 min; m/z [M+H]+ 264.

후처리

  1. customthe mixture was purged with nitrogen
  2. additionwas added
  3. customThe mixture was purged with nitrogen
  4. customsealed
  5. customThe solvents were removed
  6. customthe residue was partitioned between ethyl acetate and 2N NaOH
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe crude reaction mixture
  12. customwas purified by column chromatography (SiO2)
  13. washeluting with a mixture of dichloromethane (90 ml)

출처 및 근거

ORD 기록
ord-7d1888a7b8be4c5a8960c4f9eedc1b1f
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691806B2

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