Methyl iodide → Imidazo[1,2-a]pyridine-6-carbonitrile, 3-(methoxymethyl)-

HRID 876832Notes

Reaction equation

HRID 876832 reaction equation
[OH:1][CH2:2][C:3]1[N:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]2=[N:5][CH:4]=1.[H-].[Na+].CI.[C:18]([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:18][O:1][CH2:2][C:3]1[N:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]2=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 673059313-(Hydroxymethyl)imidazo[1,2-a]pyridine-6-carbonitrile

Product 1

HCID 67305506Imidazo[1,2-a]pyridine-6-carbonitrile, 3-(methoxymethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(hydroxymethyl)-imidazo[1,2-a]pyridine-6-carbonitrile (7-2) (346 mg, 2 mmol) in 20 mL of THF was added sodium hydride (240 mg, 60% in oil) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then methyl iodide (615 mg, 4.3 mmol) was added. The reaction was stirred at room temperature overnight. The mixture was treated with aqueous Na2CO3, then concentrated. The residue was diluted with water and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated to afford the title compound (300 mg). MS (m/z): 188.0 (M+H)+

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64d87714e81746d1820b5922727f1ab6
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…