Methyl iodide → HCID 11716765, compound

HRID 2067931Notes

Reaction equation

HRID 2067931 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH:23]([N-]C(C)C)(C)C.[Li+].IC>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:14]=2[CH3:23])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 86595318HCID 86595318, compound

Product 1

HCID 11716765HCID 11716765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

This compound was prepared according to the general procedure 3 as described hereinabove. 2-Chloro-4-(2-methyl-1-p-tolyl-1H-imidazol-4-ylethynyl)-pyridine (220 mg, 0.71 mmol) was dissolved in 5 mL THF and cooled to −75° C. Lithiumdiisopropylamide (0.61 ml, 1.22 mmol) was added, and the mixture stirred for 15 min at −75° C. Iodomethane (0.08 ml, 1.14 mmol) was added and stirring was continued at −75° C. for 2 hrs. The reaction mixture was quenched with sat. NaHCO3− solution and extracted with water and ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethylacetate 90:10→0:100 gradient) and by recrystallization from dichloromethane and diisopropylether. The desired compound was obtained as a light yellow solid (30 mg, 13%), MS: m/e=322.3 (M+H+).

Workup

  1. customThis compound was prepared
  2. stirringstirring
  3. waitwas continued at −75° C. for 2 hrs
  4. customThe reaction mixture was quenched with sat. NaHCO3− solution
  5. extractionextracted with water and ethyl acetate
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on silica gel (heptane/ethylacetate 90:10→0:100 gradient) and by recrystallization from dichloromethane and diisopropylether

Sources & evidence

ORD record
ord-fe0b3f0f9abb45798590452688e91f27
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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