Triethylamine → 4-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoic acid

HRID 2371061ノート

反応式

HRID 2371061 の反応式
[F:1][C:2]([F:20])([F:19])[CH:3]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.I[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([C:31]([F:34])([F:33])[F:32])[CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[O:18]=[C:15]([NH:14][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[CH:5]=1)[C:2]([F:19])([F:20])[F:1])/[CH:16]=[CH:17]/[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([C:31]([F:32])([F:34])[F:33])[CH:23]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 177333644-Iodo-2-(trifluoromethyl)benzoic acidHCID 86653067N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide

生成物 1

HCID 866530664-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoic acid

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Under argon, first 3.34 g (7.90 mmol) of N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide from Example 2. Stage 1, and then 2.49 g (7.90 mmol) of 4-iodo-2-(trifluoromethyl)benzoic acid (commercially available, CAS Registry Number: 954815-11-3), 0.206 g (7.90 mmol) of triphenylphosphine, 88.4 mg (0.39 nmol) of palladium(II) acetate and 13.5 g (133 mmol) of triethylamine were initially charged in 67 ml of N,N-dimethylformamide, and the reaction mixture was stirred at 100° C., for 5 hours. After addition of water, the solution was extracted with ethyl acetate, and then the organic phase was washed three times with saturated sodium chloride solution and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate.

後処理

  1. extractionthe solution was extracted with ethyl acetate
  2. washthe organic phase was washed three times with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was chromatographed on silica gel with ethyl acetate

出典と根拠

ORDレコード
ord-02c9469d2fc941ac8a1b156a84de9720
出典データセット
uspto-grants-2014_04
特許番号
US08710242B2

反応ノート

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