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Triethylamine → 8-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinoline

HRID 1174669
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174669
[CH3:1][C:2]1[C:3]([C:12]([C:14]2[N:15]=[CH:16][N:17]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C[Mg+].[Br-].[CH3:41]CN(CC)CC.CS(Cl)(=O)=O>C1COCC1.C(Cl)Cl>[CH3:1][C:2]1[C:3]([C:12]([C:14]2[N:15]=[CH:16][N:17]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=2)=[CH2:41])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59749533(8-methylquinolin-7-yl)(1-trityl-1H-imidazol-4-yl)methanoneHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 597495448-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinolineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (8-methylquinolin-7-yl)(1-trityl-1H-imidazol-4-yl)methanone (Intermediate M4) (3.59 g, 7.49 mmol) in THF (100 mL) at 0° C. was treated with MeMgBr (5.0 mL, 3M in ether) for 16 h. The reaction mixture was quenched with NH4Cl (aq) and extracted with EtOAc. The layers were separated and dried over MgSO4, filtered, evaporated and purified by column chromatography on silica gel with 3 to 4% NH3-MeOH. The alcohol in CH2Cl2 (100 mL) was treated with Et3N (8.4 mL, 60.3 mmol) and methane sulfonyl chloride (1.75 mL, 22.6 mmol) at 0° C. for 3 h. The mixture was quenched with water and extracted with CH2Cl2. The organic layers were pooled and evaporated to give 8-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinoline (Intermediate M5) 2.14 g (60% over two steps). This material was used in the next step without further purification.

Aufarbeitung

  1. customThe reaction mixture was quenched with NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. customThe layers were separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by column chromatography on silica gel with 3 to 4% NH3-MeOH
  8. customThe mixture was quenched with water
  9. extractionextracted with CH2Cl2
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ec112743288448b8a74f3ef2646dbc3a
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838545B2

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