Iodine → HCID 71279920, compound

HRID 246345Notes

Reaction equation

HRID 246345 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(=O)(O)[O-].[Na+].[I:15]I>CCO.O>[I:15][C:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 3

HCID 807IodineHCID 274090Imidazo(1,5-a)pyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 71279920HCID 71279920, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of imidazo[1,5-a]pyridine (0.50 g, 4.23 mmol) in EtOH (8 mL) and water (4 mL) was added sodium bicarbonate (1.07 g, 12.7 mmol) followed by iodine (1.61 g, 6.35 mmol). The dark maroon-brown heterogeneous reaction mixture was stirred at room temperature overnight then quenched with aqueous 10% Na2S2O3, diluted with water and extracted with EtOAc (3×). The combined organics were washed with water, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 20% to 50% EtOAc/hexanes to afford 649 mg (63%) of 1-iodo-imidazo[1,5-a]pyridine as a light brown solid (light sensitive). 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.13 (s, 1H), 7.92 (d, J=6.8 Hz, 1H), 7.33 (d, J=9.4 Hz, 1H), 6.80 (dd, J=9.4, 6.8 Hz, 1H), 6.56-6.69 (m, 1H).

Workup

  1. customthen quenched with aqueous 10% Na2S2O3
  2. additiondiluted with water
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography with 20% to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-307e2fbf3d7141c1a84e2ad232cbaab9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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