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

HRID 1955010Notes

Reaction equation

HRID 1955010 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].[C:14]([O:18][C:19]([NH:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl)=[O:20])([CH3:17])([CH3:16])[CH3:15].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:14]([O:18][C:19]([NH:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24][O:12][C:11]1[C:6]2[N:7]([C:3]([CH:1]=[O:2])=[C:4]([CH3:13])[N:5]=2)[CH:8]=[CH:9][CH:10]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143684822-Tert-butoxycarbonylamino-6-methylbenzylchlorideHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 232941628-(2-tert-Butoxycarbonylamino-6-methylbenzyloxy)-3-formyl-2-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Starting from 3-formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine (2.4 g), 2-tert-butoxycarbonylamino-6-methylbenzyl chloride (4.2 g), sodium iodide (2.5 g) and sodium carbonate (3.7 g) in acetone (400 ml) analogously using the process of Example B1 gives, after recrystallization from diisopropyl ether/ethyl acetate, 4.4 g (80%) of the title compound of m.p. 189-191° C.

Workup

  1. customgives
  2. customafter recrystallization from diisopropyl ether/ethyl acetate, 4.4 g (80%) of the title compound of m.p. 189-191° C.

Sources & evidence

ORD record
ord-bb9010412ef94799bef0638be7f77116
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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