Iodine → 6-Fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine

HRID 245874Notes

Reaction equation

HRID 245874 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:7]=1.O.C(=O)(O)[O-].[Na+].[I:19]I>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][CH3:12])=[N:9][C:10]=2[I:19])[CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 516892Sodium BicarbonateHCID 866779116-Fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine

Product 1

HCID 712803106-Fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round-bottomed flask, 6-fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine (178 mg, 0.88 mmol) was dissolved in ethanol (1.6 ml). Water (0.8 ml), sodium bicarbonate (278 mg, 3.31 mmol) and iodine (312 mg, 1.23 mmol) were added. The dark brown suspension was stirred at room temperature overnight then quenched with 10% aqueous Na2S2O3 and extracted with EtOAc (2×). The combined organic layers were washed with 10% aqueous Na2S2O3, water, and brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on silica gel and chromatographed with EtOAc/hexanes (gradient 0-10% EtOAc) to afford 110 mg (41%) of 6-fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine as a brown solid.

Workup

  1. customthen quenched with 10% aqueous Na2S2O3
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with 10% aqueous Na2S2O3, 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 0-10% EtOAc)

Sources & evidence

ORD record
ord-13c85eb8bfd543448abf04ec99743112
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…