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

HRID 1890584
Notes
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Reaction equation

HRID 1890584 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 673055063-(Methoxymethyl)imidazo[1,2-a]pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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-f9be21dda1bf492da899089ddf4e6f1f
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507487B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes