Isobutyronitrile → 2-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

HRID 385716Notes

Reaction equation

HRID 385716 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][CH:10]([CH3:13])[C:11]#[N:12].C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]([CH3:13])([CH3:9])[C:11]#[N:12])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 6559IsobutyronitrileHCID 693532,5-DibromopyridineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 115866222-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

Conditions

Temperature
70 °C

Procedure

2,5-Dibromopyridine (2 g, 8.44 mmol) was placed in a vial that was evacuated and backfilled with argon three times. Anhydrous dioxane (8.4 ml) was then added and the suspension was stirred. In a separate vial, 2-methylpropanenitrile (0.76 ml, 8.44 mmol) was added to a solution of sodium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (28.1 ml of 0.6 M in toluene, 16.9 mmol). This was stirred for 10 minutes then added to the suspension. The reaction was heated to 70° C. for 1.5 hours. It was then cooled to room temperature, quenched with water, and extracted with ethyl acetate. Purification was performed via silica gel chromatography (0-75% ethyl acetate in hexane) to yield the title compound.

Workup

  1. customwas evacuated
  2. additionAnhydrous dioxane (8.4 ml) was then added
  3. stirringThis was stirred for 10 minutes
  4. additionthen added to the suspension
  5. temperatureIt was then cooled to room temperature
  6. customquenched with water
  7. extractionextracted with ethyl acetate
  8. customPurification

Sources & evidence

ORD record
ord-33fffe6476bb4c1c9eb91e0e8e4e248e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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