N-Iodosuccinimide → 8-(Benzyloxy)-3-iodoimidazo[1,2-a]pyridine

HRID 1916035Notes

Reaction equation

HRID 1916035 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[C:18]2[N:19]([CH:23]=[CH:24][N:25]=2)[CH:20]=[CH:21][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[CH2:9]([O:16][C:17]1[C:18]2[N:19]([C:23]([I:1])=[CH:24][N:25]=2)[CH:20]=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 134329748-(Benzyloxy)imidazo[1,2-a]pyridine2×

Product 1

HCID 573552438-(Benzyloxy)-3-iodoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As shown in FIG. 6, N-iodosuccinimide (7.0 g, 31.2 mmol) was added to a solution of 8-benzyloxy-imidazo[1,2-α]pyridine (Example 19) 24 (7.0 g, 31.2 mmol) in dry acetonitrile (100 mL) at 0° C. The reaction was warmed to room temperature and then stirred for 12 hours. The mixture was filtered and the cake washed with acetonitrile and water and dried under high vacuum to afford 8-benzyloxy-3-iodo-imidazo[1,2-α]pyridine 31 as colorless solid. 9.0 g, 83%, yield.

Workup

  1. filtrationThe mixture was filtered
  2. washthe cake washed with acetonitrile and water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-84648b43d76f481d941e1350468789d4
Source dataset
uspto-grants-2013_12
Patent number
US08618079B2

Reaction notes

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