2-Amino-3-methylpyridine → 2-(4-Iodophenyl)-8-methylimidazo[1,2-a]pyridine

HRID 222895

Reaction equation

HRID 222895 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[I:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:12]=[C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]3[CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 153472-Amino-3-methylpyridineHCID 2565722-Bromo-1-(4-iodophenyl)ethanoneHCID 516892Sodium Bicarbonate

Product 1

HCID 173895682-(4-Iodophenyl)-8-methylimidazo[1,2-a]pyridineYield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of crude 2-bromo-1-(4-iodophenyl)ethanone (18.2 g), 2-amino-3-picoline (1.1 equiv, 61.6 mmol), and sodium bicarbonate (1.3 equiv, 72.8 mmol) in isopropanol (160 mL) was heated at 80° C. for 16 h. After concentrating the reaction mixture in vacuo, water (100 mL) was added and the resultant tan slurry was filtered, rinsing with water (2×50 mL). The brown solid was recrystallized from hot isopropanol and further dried in vacuo to provide the title product as a brown solid (13.2 g, 71%). ESMS [M+H]+: 335.0.

Workup

  1. concentrationAfter concentrating the reaction mixture in vacuo, water (100 mL)
  2. additionwas added
  3. filtrationthe resultant tan slurry was filtered
  4. washrinsing with water (2×50 mL)
  5. customThe brown solid was recrystallized from hot isopropanol
  6. customfurther dried in vacuo

Sources & evidence

ORD record
ord-1a97bbeac4794d80a85838c101333974
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Linked notes

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