2-Pyridinamine, 5-iodo- → HCID 77985001, compound

HRID 1502647Notes

Reaction equation

HRID 1502647 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[N:9][CH:10]=1)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][N:18]=1>C(#N)C>[I:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([CH:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([N:11]4[CH:15]=[CH:14][N:13]=[CH:12]4)=[N:9][CH:10]=3)[N:16]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 58910475HCID 58910475, compound

Product 1

HCID 77985001HCID 77985001, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

24.3 mg (corresponding to 0.0876 mmol) of 5-(2-bromoacetyl)-2-(1H-imidazole-1-yl)pyridine and 19.3 mg (corresponding to 0.0876 mmol) of 2-amino-5-iodopyridine were dissolved in 2.0 mL of acetonitrile. The resulting solution was heated under reflux for 1.5 hours in an oil bath at 100° C. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 2 mL of water and 2 mL of methanol. Then, about 1 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 10 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain crude crystals of 6-iodo-2-[2-(1H-imidazole-1-yl)pyridine-5-yl]imidazo[1,2-a]pyridine. The resulting crude crystals were purified by flash silica gel column chromatography (elution solvent: ethyl acetate/methanol=10/1), to obtain 17.7 mg (corresponding to 0.046 mmol) of 6-iodo-2-[2-(1H-imidazole-1-yl)pyridine-5-yl]imidazo[1,2-a]pyridine (FIG. 3, step 3).

Workup

  1. temperatureThe resulting solution was heated
  2. customAfter the completion of the reaction
  3. temperaturethe reaction solution was cooled down to room temperature
  4. customprecipitates
  5. filtrationwere filtered
  6. washThe precipitates were washed with acetonitrile
  7. customdried under reduced pressure
  8. additionThen, about 1 mL of a saturated sodium hydrogencarbonate solution was added
  9. customthe mixture was sonicated for 10 minutes
  10. customPrecipitates
  11. filtrationwere filtered
  12. customrecovered from the resulting mixture
  13. washsufficiently washed with water
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-9017d344f81a4d3fae3471534e138ca8
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

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