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

HRID 924689ノート

反応式

HRID 924689 の反応式
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

参加物

8

反応物 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)

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418851HCID 178418851、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
135 °C

実験手順

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, 11 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.

後処理

  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)

出典と根拠

ORDレコード
ord-6fa1fd2224354fa99eea5f628ca172ae
出典データセット
uspto-grants-2016_03
特許番号
US09283226B2

反応ノート

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