Methyl iodide → HCID 10357740, compound

HRID 860161Notes

Reaction equation

HRID 860161 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=3)[N:22]=[C:21]2[CH3:34])=[CH:16][CH:15]=1.CI>O1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH3:1])=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=3)[N:22]=[C:21]2[CH3:34])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 100856604-[1-(4-Fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-2-methyl-pyridineHCID 178418339Butyllithium

Product 1

HCID 10357740HCID 10357740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylamine (0.260 mg, 2.6 mmol) was dissolved in 5 mL dry tetrahydrofurane, n-butyllithium (1.6 mL, 1.6 M in hexane, 2.6 mmol) were added at −78° C. and the mixture was kept at −78° C. for 10 min. 4-[1-(4-Fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-2-methyl-pyridine (1) (500 mg, 1.72 mmol) in 5 mL dry tetrahydrofurane was added at −78° C. and stirring was continued for 45 min at this temperature. Methyl iodide (410 mg, 2.9 mmol) was added at −78° C. and the reaction mixture was slowly warmed to RT. The reaction mixture was quenched by addition of 50 mL water and extracted three times with diethylether (100 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (methylenchloride/methanol 9:1) and the desired compound was obtained as a white solid (325 mg, 62%), MS: m/e=306.4 (M+H+).

Workup

  1. waitwas continued for 45 min at this temperature
  2. customThe reaction mixture was quenched by addition of 50 mL water
  3. extractionextracted three times with diethylether (100 mL each)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel (methylenchloride/methanol 9:1)

Sources & evidence

ORD record
ord-600345531dc54b53a11e11f544f953ea
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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