Sodium Hydroxide → (2-methylimidazo[1,2-a]pyridin-3-yl)methanol

HRID 856659Notes

Reaction equation

HRID 856659 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[C:17](OCC)=[O:18].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[CH2:17][OH:18]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 743829ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7060539(2-methylimidazo[1,2-a]pyridin-3-yl)methanolYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, to a suspension of aluminum lithium hydride (1.6 g) in THF (100 ml) was added dropwise a solution of ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (8.56 g) in THF (100 ml) at 0° C. under nitrogen atmosphere. The mixture was stirred for 1 hour at 0° C., water (1.6 ml), 15% aqueous solution of sodium hydroxide (1.6 ml) and water (4.8 ml) were sequentially and slowly added dropwise to the solution, and the mixture was stirred for 2 hours at room temperature. To the reaction solution was added magnesium sulfate, and the precipitates were removed by filtration. The mixture was concentrated under reduced pressure, to give 2-methylimidazo[1,2-a]pyridine-3-methanol (6.45 g) as pale yellow amorphous. A mixture of 2-methylimidazo[1,2-a]pyridine-3-methanol (1 g) and 4-aminothiophenol (0.65 g) in concentrated hydrochloric acid (10 ml) was stirred for 18 hours at room temperature. 8N aqueous solution of sodium hydroxide was added to adjust pH to 10 at 0° C. and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethanol:ethyl acetate 1:4), to give 3-(4-aminophenylthiomethyl)-2-methylimidazo[1,2-a]pyridine (311 mg) as colorless crystals.

Workup

  1. additionslowly added dropwise to the solution
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customthe precipitates were removed by filtration
  4. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-17b8a1a04c954c40b016adf91dcb5af9
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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