Potassium Carbonate → HCID 44549958、化合物

HRID 2382089ノート

反応式

HRID 2382089 の反応式
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1I)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:3][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[NH:4][CH:1]=1

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 68555340Allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine

生成物 1

HCID 44549958HCID 44549958、化合物収率 37.6%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine (1.75 g, 5.35 mmol), tetrabutylammonium chloride (1.68 g, 5.35 mmol), palladium acetate (120 mg, 0.54 mmol) and potassium carbonate (2.22 g, 16.0 mmol) in DMF (50 mL) is heated at 80° C. for 1.5 h. The reaction is quenched with water and extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-5-trifluoromethyl-1H-indole (401 mg). 1H NMR (300 MHz, CDCl3): δ=8.09 (broad s, 1H), 7.90 (s, 1 H), 7.44 (s, 1H), 7.10 (s, 1H), 2.38 (s, 3H).

後処理

  1. customThe reaction is quenched with water
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

出典と根拠

ORDレコード
ord-087997e9c5fa424bafb481f40de183ad
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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