2-Bromopropanal → 8-(Acetoxymethyl)-3-methylimidazo[1,2-a]pyridine

HRID 1789206Notes

Reaction equation

HRID 1789206 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2].Br[CH:14]([CH3:17])[CH:15]=O>>[C:1]([O:4][CH2:5][C:6]1[C:7]2[N:8]([C:14]([CH3:17])=[CH:15][N:12]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 3506242-BromopropanalHCID 201888553-(Acetoxymethyl)-2-pyridinamine

Product 1

HCID 201888528-(Acetoxymethyl)-3-methylimidazo[1,2-a]pyridineYield 37.5%

Procedure

A mixture of 5.0 g (30 mmole) of 3-(acetoxymethyl)-2-pyridinamine and 4.8 g (35 mmole) of 2-bromopropanal spontaneously heated upon mixing. After cooling, the mixture was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel (using ethanol-dichloromethane as eluent) yielded 2.3 g of 8-(acetoxymethyl)-3-methylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra and by elemental analysis. [Calcd. for C11H12N2O2 : C, 64.69; H, 5.92; N, 13.72. Found: C, 63.70; H, 5.85; N, 14.24). A mixture of 2.3 g (11 mmole) of 8-(acetoxymethyl)-3-methylimidazo[1,2-a]pyridine and 1.65 g (11 mmole) of 2-mercaptobenzimidazole in 40 ml of 15% hydrogen bromide in acetic acid was heated on a steam bath. After being cooled to room temperature, the mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to an oil. Chromatography yielded 2.1 g of the title compound. Structure assignment was supported by the nmr and infrared spectra.

Workup

  1. temperaturespontaneously heated
  2. additionupon mixing
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between aqueous potassium carbonate and dichloromethane
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d40358b53004bc19e0580dfc4e6614b
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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