Ethanol → 3-Iodo-7-pyridin-4-yl-imidazo[1,2-a]pyridine

HRID 1446666Notes

Reaction equation

HRID 1446666 reaction equation
N#N.[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]3[CH:15]=[CH:16][N:17]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.C1C(=O)N([I:25])C(=O)C1.CCO>CCOC(C)=O>[I:25][C:15]1[N:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][N:3]=[CH:8][CH:7]=3)=[CH:10][C:11]2=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 947NitrogenHCID 120273N-Iodosuccinimide2×HCID 685456367-Pyridin-4-yl-imidazo[1,2-a]pyridine

Product 1

HCID 685421433-Iodo-7-pyridin-4-yl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Charge a 250 μL round bottom flask equipped with: a magnetic stirrer, temperature controlled heating mantle, N2 atmosphere, with 7-pyridin-4-yl-imidazo[1,2-a]pyridine (3.35 g, 17.2 mmol), NIS (3.8 g, 16.8 mmol), EtOH (3A). Heat the reaction to 65° C. for 1 hour. This can be followed by SiO2 TLC (100% EtOAc). Add more NIS (3.8 g, 16.8 mmol) and heat the reaction to 65° C. for 1 hour. Mix the reaction while cooling in an ice bath for 30 minutes then filter and rinse the solids with MeOH. Air dry the solids and vacuum oven dry at 40° C. to afford 4.59 g (83%). Additional product can be obtained from the filtrate. MS (ES), m/z 322 (M+1).

Workup

  1. additionCharge a 250 μL round bottom flask
  2. customequipped with: a magnetic stirrer
  3. temperatureHeat
  4. customthe reaction to 65° C. for 1 hour
  5. temperatureheat
  6. customthe reaction to 65° C. for 1 hour
  7. additionMix
  8. customthe reaction
  9. temperaturewhile cooling in an ice bath for 30 minutes
  10. filtrationthen filter
  11. washrinse the solids with MeOH
  12. customAir dry the solids and vacuum oven
  13. customdry at 40° C.
  14. customto afford 4.59 g (83%)
  15. customAdditional product can be obtained from the filtrate

Sources & evidence

ORD record
ord-d541856da8ed4ffdbc3edd78a33d5676
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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