Sodium Iodide → 8-{2-[(2-Methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde

HRID 862552Notes

Reaction equation

HRID 862552 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1[NH:31][C:32](=[O:38])[O:33][CH2:34][CH2:35][O:36][CH3:37]>CC(C)=O>[CH3:37][O:36][CH2:35][CH2:34][O:33][C:32]([NH:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:24]=1[CH2:23][O:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:38]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridineHCID 538354172-Methoxyethyl 2-chloromethyl-3-methylphenylcarbamate

Product 1

HCID 196985318-{2-[(2-Methoxyethoxy)carbonylamino]-6-methylbenzyloxy}-2-methylimidazo[1,2-a]pyridine-3-carboxaldehydeYield 86.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g (11.35 mmol) of 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde, 1.2 g of anhydrous sodium carbonate, 0.17 g (1.14 mmol) of sodium iodide and 3.3 g (12.8 mmol) of 2-methoxyethyl 2-chloromethyl-3-methylphenylcarbamate in 30 ml of acetone is stirred at RT for 24 h and poured onto 200 ml of ice-water. The precipitate is filtered off, dried and recrystallized from toluene/diisopropyl ether. 3.9 g (86.5%) of the title compound of m.p. 119°-120° C. are obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. customdried
  3. customrecrystallized from toluene/diisopropyl ether

Sources & evidence

ORD record
ord-b0fc08656715420f8288fdcc1f33f65c
Source dataset
uspto-grants-1998_02
Patent number
US05719161

Reaction notes

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