HCID 59751465, compound → Ammonia methanol

HRID 748655Notes

Reaction equation

HRID 748655 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)=[O:12])=[CH:3][CH:2]=1.[CH3:37][Mg+].[Br-]>C1COCC1.CCOCC>[NH3:1].[CH3:11][OH:12].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)([OH:12])[CH3:37])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 59751465HCID 59751465, compoundHCID 178418689HCID 178418689, compound

Product 2

HCID 21705897Ammonia methanolYield 5%HCID 59751464HCID 59751464, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of quinolin-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate G2) (13.1 mmol) in THF (100 mL) at 0° C. was treated with MeMgBr (9.0 mL, 27 mmol of a 3M solution in Et2O) for 45 m. The mixture was quenched with a sat. solution of NH4Cl and water. The layers were separated and the organic layer dried over MgSO4. The suspension was filtered and evaporated to dryness. The material was purified by chromatography on SiO2 with 50% EtOAc:hexane to 5% NH3-MeOH: dichloromethane to give 1-quinolin-4-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate G3) 5.69 g.

Workup

  1. customThe mixture was quenched with a sat. solution of NH4Cl and water
  2. customThe layers were separated
  3. dry with materialthe organic layer dried over MgSO4
  4. filtrationThe suspension was filtered
  5. customevaporated to dryness
  6. customThe material was purified by chromatography on SiO2 with 50% EtOAc

Sources & evidence

ORD record
ord-69e797641aee4badb289cf4ced00daf4
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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