p-Fluorophenethylamine → 4-tert-butyl-2-chloro-N-[2-(4-fluoro-phenyl)-ethyl]-benzamide

HRID 855251노트

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HRID 855251 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]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][NH2:29])=[CH:23][CH:22]=1.CN([CH:33]=[O:34])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:33]([NH:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[O:34])=[C:7]([Cl:19])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 4653p-FluorophenethylamineHCID 6228DimethylformamideHCID 17859607Trifluoro-methanesulfonic acid 4-tert-butyl-2-chloro-phenyl ester

생성물 1

HCID 693426474-tert-butyl-2-chloro-N-[2-(4-fluoro-phenyl)-ethyl]-benzamide수율 59%

시약·촉매·용매 2

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

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온도
70 °C

실험 절차

317 mg (1 mmol) of trifluoro-methanesulfonic acid 4-tert-butyl-2-chloro-phenyl ester and 281 mg (2 mmol) of 2-(4-fluoro-phenyl) ethyl amine were dissolved in 5 ml DMF. Under argon at rt 6.7 mg (0.03 mmol) of palladium acetate and 12.4 mg (0.03 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 198 mg (59%) of 4-tert-butyl-2-chloro-N-[2-(4-fluoro-phenyl)-ethyl]-benzamide as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.41 (t, 1H), 7.42 (s, 1H), 7.39 (d, 1H), 7.30 (d, 1H), 7.28 (t, 2H), 7.12 (t, 2H), 3.43 (q, 2H), 2.81 (t, 2H), 1.27 (s, 1H).

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-224f92cee91345d780ad350f92261fa6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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