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

HRID 1729446Notes

Reaction equation

HRID 1729446 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. 1H NMR (250 MHz, CD3OD) δ 8.28 (d, 1H, J=6 Hz), 7.72-7.65 (m, 2H), 7.62-7.54 (m, 2H), 7.22 (d, 1H, J=6 Hz), 7.17-7.08 (AB q, 4H), 5.61 (s, 2H), 3.12 (q, 2H, J=9 Hz), 2.89 (t, 2H, J=9 Hz), 1.80-1.63 (m, 2H), 1.41 (t, 3H, J=9 Hz), 0.99 (t, 3H, J=9 Hz).

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-246748e3a1ff47048a6216b89dcc98c6
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

Loading…