Dimethylformamide → 4-tert-butyl-2-chloro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 855253노트

반응식

HRID 855253 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8](OS(C(F)(F)F)(=O)=O)=[C:7]([Cl:19])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH2:30])[CH:25]=[CH:26][CH:27]=1.CN([CH:36]=[O:37])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:36]([NH:30][CH2:29][CH2:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:31])([F:32])[F:20])[CH:23]=2)=[O:37])=[C:7]([Cl:19])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 104223Phenethylamine, m-trifluoromethyl-HCID 17859607Trifluoro-methanesulfonic acid 4-tert-butyl-2-chloro-phenyl ester

생성물 1

HCID 693465104-tert-butyl-2-chloro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide수율 39%

시약·촉매·용매 2

HCID 812191,3-Bis(diphenylphosphino)propane촉매HCID 167845palladium(II) acetate촉매

반응 조건

온도
70 °C

실험 절차

633 mg (2 mmol) of trifluoro-methanesulfonic acid 4-tert-butyl-2-chloro-phenyl ester (prepared as described in example S80) and 416 mg (2.2 mmol) of 2-(3-trifluoromethyl-phenyl) ethyl amine were dissolved in 10 ml DMF. Under argon at rt 13.4 mg (0.06 mmol) of palladium acetate and 24.8 mg (0.06 mmol) of dppp were added. The reaction mixture was evacuated and charged with carbon monoxide gas three times. The reaction mixture was heated to 70° C. under a carbon monoxide atmosphere for 1 h. Water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed with 1N aqueous HCl solution, once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (45 g silica gel, heptane/EtOAc 7:3) to yield 298 mg (39%) of 4-tert-butyl-2-chloro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide as a light yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.43 (t, 1H), 7.61-7.55 (m, 4H), 7.41 (s, 1H), 7.36 (d, 2H), 7.22 (d, 1H), 3.50 (q, 2H), 2.93 (t, 2H), 1.27 (s, 9H).

후처리

  1. customThe reaction mixture was evacuated
  2. additioncharged with carbon monoxide gas three times
  3. additionWater was added
  4. extractionthe reaction mixture was extracted twice with EtOAc
  5. washThe combined organic layers were washed with 1N aqueous HCl solution, once with saturated aqueous NaCl solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography (45 g silica gel, heptane/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-d495b0f6db994c199514bea746bbca6c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

반응 노트

불러오는 중…