Chloroacetaldehyde → 7-(2-Methoxyethoxy)imidazo[1,2-a]pyridine

HRID 1095665Notes

Reaction equation

HRID 1095665 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=1.Cl[CH2:14][CH:15]=O>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[CH:14]=[CH:15][N:12]=[C:8]2[CH:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 667820424-(2-Methoxyethoxy)pyridin-2-amine

Product 1

HCID 583692597-(2-Methoxyethoxy)imidazo[1,2-a]pyridineYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-(2-methoxyethoxy)pyridin-2-amine (20.0 g, 119 mmol), 2-chloroacetaldehyde (32.2 ml, 250 mmol) and tetrahydrofuran (100 mL) were heated in a sealed tube to 75° C. over 3 days. The reaction mixture was concentrated under reduced pressure and dissolved in ethyl acetate. The resulting solution was washed twice sodium bicarbonate. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to yield title compound (23.5 g, quantitative yield) MS APCI (+) m/z 193 (M+1) detected.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washThe resulting solution was washed twice sodium bicarbonate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a129b452fe7494f8c0db2af84f28a92
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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