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

HRID 1243898
ノート
印刷プレビュー

反応式

HRID 1243898 の反応式
[Cl-].[F:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Zn+])=[CH:5][CH:4]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:23](=[O:39])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:26][CH:25]=1)=[C:18](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:16]2>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C1COCC1.CN1C(=O)CCC1.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]>[F:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH3:11])[CH:14]=3)[C:19]=2[C:23]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:26][CH:25]=2)=[O:39])=[CH:5][CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 11685250Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl esterHCID 178505764HCID 178505764、化合物

生成物 1

HCID 10481006[2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone収率 78%

試薬・触媒・溶媒 4

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

実験手順

Add 4-fluorobenzylzinc chloride (4 mL of 0.5 M/THF) to a stirred solution of trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (525 mg), Pd(dba)2 (68 mg), dppf (66 mg) and Bu4NI (1.1 g) in THF/NMP (2 mL/1.5 mL) at room temperature. Heat the mixture to reflux for 2 h and quench with water. Dilute the mixture with CH2Cl2 and wash with water and brine, dry over MgSO4, filter and concentrate. Load the crude product on an SCX cartridge, wash with MeOH and elute the product with 2M NH3/MeOH. Purify the product by flash chromatography (0–5% (2M NH3 in MeOH/CH2Cl2) to afford [2-(4-fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (380 mg, 78%)

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux for 2 h
  3. customquench with water
  4. additionDilute the mixture with CH2Cl2
  5. washwash 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 the product with 2M NH3/MeOH
  11. customPurify the product by flash chromatography (0–5% (2M NH3 in MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-2d5e7b27f2e94b53a9fa0fd7dd229beb
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07119206B2

反応ノート

読み込み中…

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