N-Iodosuccinimide → 8-(Benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine

HRID 456716

Reaction equation

HRID 456716 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:25]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([I:25])=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 184367148-(Benzyloxy)-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 184367138-(Benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 0° C. solution of 8-(benzyloxy)-2-(4-fluorophenyl)imidazo[1,2-a]pyridine (0.25 g, 0.79 mmol) in N,N-dimethylformamide (8.0 mL) was added dropwise a solution of N-iodosuccinimide (0.17 g, 0.79 mmol) in N,N-dimethylformamide (4 mL). The reaction was stirred for 2.5 hours and concentrated to a volume of 2 mL The mixture was diluted with ethyl acetate, washed twice with 1M aqueous sodium hydroxide, and concentrated. The residue was purified by silica gel chromatography, eluting with 5% acetone in dichloromethane to yield 0.23 (67%) of 8-(benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine. 1H NMR (CDCl3): δ 8.10 (dd, 2H), 7.90 (d, 1H), 7.53 (d, 2H), 7.40 (m, 3H), 7.19 (t, 2H), 6.81 (t, 1H), 6.61 (d, 1H), 5.46 (s, 2H); MS m/z 445 (M+1).

Workup

  1. concentrationconcentrated to a volume of 2 mL The mixture
  2. additionwas diluted with ethyl acetate
  3. washwashed twice with 1M aqueous sodium hydroxide
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 5% acetone in dichloromethane

Sources & evidence

ORD record
ord-01600c0d61b74b45b7e269959c5a72b7
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Linked notes

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