Methyl iodide → 2-(4-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-methoxyethyl}phenyl)-5-fluoropyridine

HRID 216378Notes

Reaction equation

HRID 216378 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][C:8]([CH3:52])([CH2:50][CH3:51])[CH2:9][C:10]1[N:11]=[C:12]([CH2:34][CH:35]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][N:44]=3)=[CH:39][CH:38]=2)[OH:36])[N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1.CI>C(O)(C)(C)C>[CH3:7][C:8]([CH3:52])([CH2:50][CH3:51])[CH2:9][C:10]1[N:11]=[C:12]([CH2:34][CH:35]([C:37]2[CH:38]=[CH:39][C:40]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][N:44]=3)=[CH:41][CH:42]=2)[O:36][CH3:1])[N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 686683162-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

Product 1

HCID 686676522-(4-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-methoxyethyl}phenyl)-5-fluoropyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (21 mg, 0.19 mmol) was added to a solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol (104 gm, 0.17 mmol) and methyl iodide (19 μL, 0.31 mmol) in tert-butanol (17 mL) at ambient temperature. After stirring overnight, the reaction mixture was washed with brine (100 mL), dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 2-(4-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-methoxyethyl}phenyl)-5-fluoropyridine as an off-white solid.

Workup

  1. washthe reaction mixture was washed with brine (100 mL)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-566eee4b35d74f6cbc7007de671e3179
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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