Iodine → 1-Iodo-6-methylimidazo[1,5-A]pyridine

HRID 245842Notes

Reaction equation

HRID 245842 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][CH:15]=2)[CH:12]=1.[I:16]I>O.C(O)C>[I:16][C:15]1[N:14]=[CH:13][N:11]2[CH:12]=[C:7]([CH3:6])[CH:8]=[CH:9][C:10]=12

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 594583226-Methylimidazo[1,5-A]pyridine

Product 1

HCID 712806461-Iodo-6-methylimidazo[1,5-A]pyridineYield 56.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a round-bottomed flask, sodium bicarbonate (215 mg, 2.56 mmol) was suspended in water (0.6 ml) and ethanol (1.2 ml). 6-methyl-imidazo[1,5-a]pyridine (90 mg, 0.68 mmol) was added followed by iodine (242 mg, 0.95 mmol). The dark brown suspension was stirred at room temperature overnight then quenched with 10% Na2S2O3-solution and extracted with EtOAc (2×). The organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to provide 99 mg (56%) of 1-iodo-6-methyl-imidazo[1,5-a]pyridine as a light brown solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.11 (s, 1H), 7.73 (s, 1H), 7.24 (d, J=9.4 Hz, 1H), 6.67 (d, J=9.1 Hz, 1H), 2.27 (s, 3H).

Workup

  1. customthen quenched with 10% Na2S2O3-solution
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers were washed with water and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)

Sources & evidence

ORD record
ord-3d95631a474f4fda8a6c52ab8b05e973
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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