Iodine → HCID 67347968, compound

HRID 1028997Notes

Reaction equation

HRID 1028997 reaction equation
II.N1C=CC=CC=1.[I:9][C:10]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:11]=1[C:12](=S)[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C1COCC1.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>[I:9][C:10]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]2=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 807IodineHCID 1049PyridineHCID 86676842HCID 86676842, compound

Product 1

HCID 67347968HCID 67347968, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 24437Sodium SulfiteSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Iodine (0.827 g, 3.26 mmol) and pyridine (0.263 mL, 3.26 mmol) were added to 2-iodo-3-methyl-N-(pyridin-2-ylmethyl)benzothioamide (0.40 g, 1.086 mmol) in THF (2.2 mL) at 0° C. The solution was allowed to warm to RT and stirred 15 min. The reaction mixture was diluted with saturated sodium bicarbonate and aq. sodium sulfite and extracted with EtOAc. The combined organic extracts were washed with saturated sodium bicarbonate, water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:1.5 EtOAc in hexane to provide 3-(2-iodo-3-methylphenyl)imidazo[1,5-a]pyridine.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate, water, saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material
  7. customThe crude material was purified by silica gel chromatography
  8. washby eluting with 1:1.5 EtOAc in hexane

Sources & evidence

ORD record
ord-152c61a559664c9eab80590ca0ac93e3
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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