Methyl iodide → HCID 67055922, compound

HRID 2036823Notes

Reaction equation

HRID 2036823 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[N:8][CH:9]=1.[CH3:13]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[C:11]#[N:12])[CH:7]=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 67055922HCID 67055922, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (95%, 113 mg, 4.70 mmol) in DMF was added a solution of 2-(5-bromopyridin-3-yl)acetonitrile (from example 199, 0.8 g, 4 mmol) in DMF. Upon completion of addition, the reaction mixture was stirred at RT for 30 min. After this time, methyl iodide (0.3 mL, 4 mmol) was added and the stirring continued for an additional 4 h. At the conclusion of this period, the reaction mixture was quenched by addition of saturated ammonium chloride solution and then extracted into ethyl acetate. The combined organic portions were concentrated under reduced pressure and the resulting residue was purified by flash column chromatography (30% EtOAc in hexanes) to yield racemic 2-(5-bromopyridin-3-yl)propanenitrile (200 mg, 24%). 1H NMR (400 MHz, CDCL3) δ (ppm): 8.67 (d, 1H, J=2 Hz); 8.53 (d, 1H, J=5 Hz); 7.88 (t, 1H, J=5 Hz); 3.94 (q, 1H, J=7.6 Hz); 1.69 (d, 3H, J=7.6 Hz). LCMS Method Y: retention time 1.54 min; [M+1]=212.6.

Workup

  1. additionUpon completion of addition
  2. waitthe stirring continued for an additional 4 h
  3. customAt the conclusion of this period, the reaction mixture was quenched by addition of saturated ammonium chloride solution
  4. extractionextracted into ethyl acetate
  5. concentrationThe combined organic portions were concentrated under reduced pressure
  6. customthe resulting residue was purified by flash column chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1fbcc2a4ca8c487b94eabba7726a1286
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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