N-Iodosuccinimide → 3-Iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine

HRID 1253566Notes

Reaction equation

HRID 1253566 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1.[I:18]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[I:18][C:9]1[N:8]2[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][C:7]2=[N:11][CH:10]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 672069685-Methoxy-7-phenylimidazo[1,2-a]pyridine

Product 1

HCID 584048583-Iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-methoxy-7-phenylimidazo[1,2-a]pyridine (397 mg, 1.77 mmol) in acetonitrile (30 ml) was added N-iodosuccinimide (478 mg, 2.12 mmol). After 1 h the reaction mixture was diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide and water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to give 3-iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine. 1H NMR (600 MHz, DMSO-d6) δ 7.86 (d, 1H); 7.83 (d, 1H); 7.52-7.53 (m, 1H); 7.48-7.45 (m, 2H); 7.38-7.40 (m, 1H); 7.33-7.35 (m, 1H); 6.61 (d, 1H); 4.10 (s, 3H). LRMS (ESI) calculated for C14H12IN2O [M+H]+, 351.0 found 350.9.

Workup

  1. washwashed with 1N aqueous sodium hydroxide and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-51905adbd323499b890921247fbaaaa6
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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