Sodium Iodide → 8-(2-tert-Butoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1955008Notes

Reaction equation

HRID 1955008 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:13]([O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:13]([O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23][O:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143684822-Tert-butoxycarbonylamino-6-methylbenzylchlorideHCID 224679492,3-Dimethylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 232872968-(2-tert-Butoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Starting from 8-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine (1.6 g), 2-tert-butoxycarbonylamino-6-methylbenzyl chloride (3.1 g), sodium iodide (1.8 g) and sodium carbonate (2.7 g) in acetone (350 ml) analogously using the process of Example B1 gives, after chromatography on silica gel (eluent toluene/dioxane 5:1) and recrystallization from cyclohexane, 3.0 g (78%) of the title compound of m.p. 128-131° C.

Workup

  1. customgives
  2. customafter chromatography on silica gel (eluent toluene/dioxane 5:1) and recrystallization from cyclohexane, 3.0 g (78%) of the title compound of m.p. 128-131° C.

Sources & evidence

ORD record
ord-8498699a36b04a7897b1db728f9bba9c
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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