Sodium Iodide → 3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-bromobenzene

HRID 902605노트

반응식

HRID 902605 반응식
C(=O)([O-])[O-].[K+].[K+].[Na+].[I-].Br[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([Br:20])[CH:17]=[CH:18][CH:19]=1.[Cl:21][C:22]1[C:43]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:41]=[CH:40][C:23]=1[CH2:24][NH:25][CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[Cl:21][C:22]1[C:43]([C:44]([F:45])([F:46])[F:47])=[CH:42][CH:41]=[CH:40][C:23]=1[CH2:24][N:25]([CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([Br:20])[CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 193891331-Bromo-3-(3-bromopropoxy)benzeneHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

생성물 1

HCID 597014793-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-bromobenzene수율 29%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Potassium carbonate (140 mg, 1.0 mmol) and NaI (82 mg, 0.34 mmol) were added to a solution of 3-(3-bromopropoxy)bromobenzene (100 mg, 0.34 mmol), (2-chloro-3-trifluoromethylbenzyl)(2,2-diphenylethyl)amine and acetonitrile (3 mL). The mixture was heated at reflux for 16 h. The mixture was allowed to cool to RT and concentrated in vacuo. The residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers separated. The aqueous layer was extracted with methylene chloride (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: 0.1% trifluoroacetic acid in acetonitrile B: 0.1% aqueous trifluoroacetic acid, A: 10 to 90% during 10 min, UV detection at 254 nm) to give 52 mg (29%) of the title compound as an oil. MS (ESI) 639.2 [M+H]+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers
  5. customseparated
  6. extractionThe aqueous layer was extracted with methylene chloride (2×10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

출처 및 근거

ORD 기록
ord-7362dbaca0634b06b3cdb8300b47732a
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365085B2

반응 노트

불러오는 중…