Potassium Carbonate → HCID 9843152、化合物

HRID 1168221ノート

反応式

HRID 1168221 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.Cl[C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 683662STK3454632 回

生成物 1

HCID 9843152HCID 9843152、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

4-Pyridineethanamine (Maybridge Chemical Co, Cornwall, England; 0.31 g, 2.5 mmol) is added to a stirred mixture of 2-chloro-N-[3(trifluoromethyl)phenyl]-3-pyridinecarboxamide (intermediate 1a; 0.90 g, 3 mmol), powdered potassium carbonate (0.35 g, 2.5 mmol) and copper(1)iodide; 0.48 g, 2.5 mmol) in dimethylformamide (10 mL). The resulting mixture is then purged with argon and subsequently heated at 100° C. under an argon atmosphere for 2 hours. The mixture is cooled, treated with water (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extracts are washed with an aqueous solution of ammonia (2×50 mL of 10%), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate and recrystalised from ethyl acetate—hexane to give the title compound as a colourless crystalline solid, m.p. 128-138° C.

後処理

  1. customThe resulting mixture is then purged with argon
  2. temperatureThe mixture is cooled
  3. additiontreated with water (100 mL)
  4. extractionextracted with ethyl acetate (3×80 mL)
  5. washThe combined extracts are washed with an aqueous solution of ammonia (2×50 mL of 10%)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent is evaporated off under reduced pressure
  9. customto yield the crude product which
  10. customis purified by column chromatography on silica gel, eluent ethyl acetate
  11. customrecrystalised from ethyl acetate—hexane

出典と根拠

ORDレコード
ord-5cbe809527fc46d6955cf42cd11bbf3c
出典データセット
uspto-grants-2003_09
特許番号
US06624174B2

反応ノート

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