Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester → [6-Methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 2223679노트

반응식

HRID 2223679 반응식
[Cl-].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][Zn+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20]([C:24](=[O:40])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=1)=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=[CH:17]2>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN1C(=O)CCC1.C1COCC1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20]([C:24]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=1)=[O:40])=[C:19]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[O:3][CH3:2])[CH:18]=[CH:17]2

참가 물질

8

반응물 2

HCID 11685250Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl esterHCID 178489474HCID 178489474, 화합물

생성물 1

HCID 22046618[6-Methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone수율 87%

시약·촉매·용매 5

HCID 67553Tetrabutylammonium Iodide촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 6344Dichloromethane용매HCID 22156051tetrahydrofuran N-methylpyrrolidinone용매

실험 절차

Add a solution of 2-methoxybenzylzinc chloride (8 mL, 0.5 M/THF) to a mixture of trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (1.0 g, 1.86 mmol), Bu4NI (2.1 g, 5.7 mmol), Pd(dba)2 (68 mg 0.12 mmol) and dppf (66 mg, 0.12 mmol) in NMP/THF (5 mL, 3:2). Heat the mixture to reflux for 2 h. Quench the reaction with water and dilute with CH2Cl2. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Load the crude product on an SCX cartridge, wash with MeOH and elute with 2M NH3/MeOH. Purify the resulting product by flash chromatography (0-5% (2M NH3/MeOH)/CH2Cl2) to afford [6-methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (820 mg, 87%).

후처리

  1. temperatureHeat the mixture
  2. temperatureto reflux for 2 h
  3. customQuench
  4. customthe reaction with water
  5. washWash the organic phase with water and brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. washLoad the crude product on an SCX cartridge, wash with MeOH
  10. washelute with 2M NH3/MeOH
  11. customPurify the resulting product by flash chromatography (0-5% (2M NH3/MeOH)/CH2Cl2)

출처 및 근거

ORD 기록
ord-9f6f938c731d40ebbbdfa025617c33f6
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375229B2

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