Methyl iodide → 7-Ethyl-2-propylimidazo[4,5-b]pyridine

HRID 466725Notes

Reaction equation

HRID 466725 reaction equation
[C:1]([Li])(C)(C)C.[CH3:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[N:13]=[C:14]([CH2:16][CH2:17][CH3:18])[NH:15][C:8]=12.CI>C1COCC1>[CH2:6]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[N:13]=[C:14]([CH2:16][CH2:17][CH3:18])[NH:15][C:8]=12)[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 190122277-Ethyl-2-propylimidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyllithium (0.978 mL, 1.7M/pentane) was added to a cooled (-78° C.) THF (5 mL) solution of 7-methyl-2-propylimidazo[4,5-b]pyridine (97 mg, 0.554 mmol). After 2 hour the reaction was warmed to 0° C. for 1 minute then cooled back to -78° C. MeI (0.172 mL) was added, the mixture was stirred at -78° C. for 1 hour then warmed to 0° C. for 1 minute and then quenched (NH4OH). Extractive workup and purification (SiO2, 2% MeOH/ EtOAc) gave 85 mg of 7-ethyl-2-propylimidazo[4,5-b]pyridine which was converted to the title compound as outlined in Example 7, Part B.

Workup

  1. temperaturethen cooled back to -78° C
  2. temperaturethen warmed to 0° C. for 1 minute
  3. customquenched (NH4OH)
  4. customExtractive workup and purification (SiO2, 2% MeOH/ EtOAc)

Sources & evidence

ORD record
ord-984931110f754bd09971162d3a2d91c4
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Reaction notes

Loading…