Potassium Carbonate → HCID 118113997, compound

HRID 2178405Notes

Reaction equation

HRID 2178405 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=3)[C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:28]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[N:34][CH:35]=1)[CH3:29]>C(#N)C>[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:28]([C:30]4[CH:35]=[N:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[CH3:29])=[C:14]([O:19][CH3:20])[CH:13]=3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118114012HCID 118114012, compound2×HCID 118114078HCID 118114078, compound

Product 1

HCID 118113997HCID 118113997, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of 4-((6-iodo-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-2-methoxyphenol (1.32 g, 3.46 mmol) and potassium carbonate (1.30 g, 9.41 mmol) in acetonitrile (25 mL) was added 5-(1-chloroethyl)-2-methoxypyridine (0.72 g, 4.20 mmol). The mixture was heated at 100° C. After 6.5 h, an additional quantity 5-(1-chloroethyl)-2-methoxypyridine (0.300 g, 1.75 mmol) was added, and heating was continued. After 22 h, the mixture was allowed to cool to room temperature and was partitioned between water and 1:5 ethyl acetate/diethyl ether. The phases were separated, and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water, dried over magnesium sulfate, filtered, and concentrated. Chromatographic purification (40 g SiO2 column, 0-10% 0.01 M ammonia in methanol/dichlormethane elute) afforded 0.88 g (49%) of 6-iodo-3-(3-methoxy-4-(1-(6-methoxypyridin-3-yl)ethoxy)benzyl)-3H-imidazo[4,5-b]pyridine as an impure solid.

Workup

  1. temperatureheating
  2. waitAfter 22 h
  3. temperatureto cool to room temperature
  4. customwas partitioned between water and 1:5 ethyl acetate/diethyl ether
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customChromatographic purification (40 g SiO2 column, 0-10% 0.01 M ammonia in methanol/dichlormethane elute)

Sources & evidence

ORD record
ord-5ffde07515d24c5c91e8b1c5d8e9ee22
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

Loading…