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

HRID 747261Notes

Reaction equation

HRID 747261 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-70fe87400a7249b6a32c566cb9d9132c
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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