N-Iodosuccinimide → Methyl 3-iodoimidazo[1,2-a]pyridine-7-carboxylate

HRID 229441Notes

Reaction equation

HRID 229441 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH3:9][O:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]2[CH:19]=[CH:20][N:21]=[C:15]2[CH:14]=1)=[O:12]>C(#N)C>[CH3:9][O:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]2[C:19]([I:8])=[CH:20][N:21]=[C:15]2[CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylate

Product 1

HCID 57497695Methyl 3-iodoimidazo[1,2-a]pyridine-7-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NIS (1.5 eq, 1.06 mmol, 238 mg) was added in one portion to a stirred solution of imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (0.705 mmol, 124 mg) in acetonitrile (3 mL). The resulting mixture was stirred overnight. The resulting precipitate was filtered and washed with ethyl acetate. Drying in vacuo at room temperature afforded 3-iodo-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester in 88% yield. m/z (M+H)=303.1.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ethyl acetate
  3. customDrying in vacuo at room temperature

Sources & evidence

ORD record
ord-efda8afd4367441fb36d3814e5cbd0a8
Source dataset
uspto-grants-2009_07
Patent number
US07563797B2

Reaction notes

Loading…