8-(Acetoxymethyl)-3-methylimidazo[1,2-a]pyridine → 2-[[(3-methylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazole

HRID 1789207Notes

Reaction equation

HRID 1789207 reaction equation
C(O[CH2:5][C:6]1[C:7]2[N:8]([C:12]([CH3:15])=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1)(=O)C.[SH:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>Br.C(O)(=O)C>[CH3:15][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][S:16][C:17]3[NH:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=3)[C:7]2=[N:14][CH:13]=1

Participants

5

Reactant 2

HCID 201888528-(Acetoxymethyl)-3-methylimidazo[1,2-a]pyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 201888372-[[(3-methylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazoleYield 64.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

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. temperaturewas heated on a steam bath
  2. customthe mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-53c734d52032499ab6a88264f406cab5
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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