Sodium Iodide → 6-Bromo-3-carboethoxy-8-(2,6-dimethyl-4-fluorobenzylamino)-2-methylimidazo[1,2-a]pyridine

HRID 1386093Notes

Reaction equation

HRID 1386093 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:18][C:19]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([CH3:28])[C:20]=1[CH2:21]Br.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][CH2:21][C:20]2[C:19]([CH3:18])=[CH:26][C:25]([F:27])=[CH:24][C:23]=2[CH3:28])[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 217173648-Amino-6-bromo-3-carboethoxy-2-methylimidazo[1,2-a]pyridineHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Product 1

HCID 217173256-Bromo-3-carboethoxy-8-(2,6-dimethyl-4-fluorobenzylamino)-2-methylimidazo[1,2-a]pyridineYield 59.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-amino-6-bromo-3-carboethoxy-2-methylimidazo[1,2-a]pyridine (2.06 g, 6.91 mmol), 2,6-dimethyl-4-fluorobenzylbromide (1.05 g, 4.48 mmol), sodium iodide (0.45 g), sodium carbonate (2.2 g) and acetone (40 ml) was refluxed for 22 h. The reaction mixture was filtered. The filtered material was washed with CH2Cl2. The methylene chloride solution was washed with water, dried and evaporated in vacuo. The residue was suspended in ethanol/ether and filtered to give 1.15 g (56%) of the title compound.

Workup

  1. temperaturewas refluxed for 22 h
  2. filtrationThe reaction mixture was filtered
  3. washThe filtered material was washed with CH2Cl2
  4. washThe methylene chloride solution was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ef01f0ad754a4404bccebaf2acdc04de
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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