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 2223679ノート

反応式

HRID 2223679 の反応式
[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

参加物

8

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 67553Tetrabutylammonium Iodide触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 6344Dichloromethane溶媒HCID 22156051tetrahydrofuran N-methylpyrrolidinone溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9f6f938c731d40ebbbdfa025617c33f6
出典データセット
uspto-grants-2008_05
特許番号
US07375229B2

反応ノート

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