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 2371061노트

반응식

HRID 2371061 반응식
[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

참가 물질

8

반응물 4

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

생성물 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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02c9469d2fc941ac8a1b156a84de9720
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710242B2

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