Methyl iodide → HCID 86713193, compound

HRID 1500305Notes

Reaction equation

HRID 1500305 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]#[N:12])=[N:8][CH:9]=1.[CH3:13]I>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 29927881(5-Bromopyridin-2-yl)acetonitrile

Product 1

HCID 86713193HCID 86713193, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (7 mg, 0.17 mmol) is added to 2-(5-bromopyridin-2-yl)acetonitrile (300 mg, 0.15 mmol) in THF at −5° C. After 30 minutes methyl iodide is added (56 μL, 1.5 mmol) and the mixture warmed to r.t. After stirring for 4 hours, the mixture is partitioned between brine and methylene chloride. The organics were separated, dried over magnesium sulfate and the solvent removed under reduced pressure. The crude material is purified by silica gel chromatography to give the title compound (128 mg): LCMS [M+H] 196.0.

Workup

  1. customthe mixture is partitioned between brine and methylene chloride
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe crude material is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f6da73861dd24173942c3bdbba86aa29
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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