Iodine → (6-Fluoro-1-iodo-imidazo[1,5-a]pyridin-3-yl)-methanol

HRID 245853Notes

Reaction equation

HRID 245853 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[N:9][CH:10]=2)[CH:7]=1.C(=O)(O)[O-].[Na+].[I:18]I>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[N:9][C:10]=2[I:18])[CH:7]=1

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 86677906(6-Fluoro-imidazo[1,5-a]pyridin-3-yl)-methanol

Product 1

HCID 71280570(6-Fluoro-1-iodo-imidazo[1,5-a]pyridin-3-yl)-methanolYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a round-bottomed flask, (6-fluoro-imidazo[1,5-a]pyridin-3-yl)-methanol (225 mg, 1.15 mmol) was dissolved in ethanol (2 ml) and water (1 ml). Sodium bicarbonate (341 mg, 4.06 mmol) was added followed by iodine (383 mg, 1.51 mmol). The dark brown suspension was stirred at room temperature for 3 h 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 absorbed on silica gel and chromatographed with EtOAc/hexanes (gradient 0-40% EtOAc) to provide 157 mg (50%, 2 steps) of (6-fluoro-1-iodo-imidazo[1,5-a]pyridin-3-yl)-methanol as a light yellow solid.

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 absorbed on silica gel
  8. customchromatographed with EtOAc/hexanes (gradient 0-40% EtOAc)

Sources & evidence

ORD record
ord-7ec3c0ae825d4f8b96b650a10b4c9233
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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