Water → HCID 21075124, compound

HRID 1181389Notes

Reaction equation

HRID 1181389 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:3]=1.O.[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:13]#[N:14])[N:3]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 221134152-Bromo-6-tert-butylpyridine

Product 1

HCID 21075124HCID 21075124, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-6-tert-butylpyridine (Description 14; 9.9 g, 46 mmol) in anhydrous N,N-dimethylformamide (130 ml) was added zinc cyanide (6.48 g, 55.2 mmol) and Pd(PPh3)4 (2.65 g, 2.3 mmol). The mixture was degassed then heated at 80° C. overnight. The cooled reaction mixture was poured into water (500 ml), and extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with water (2×300 ml), brine (100 ml), dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica eluting with 5% Et2O in iso-hexanes to give the title compound (6.6 g, 89%).

Workup

  1. customThe mixture was degassed
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe combined organic layers were washed with water (2×300 ml), brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica eluting with 5% Et2O in iso-hexanes

Sources & evidence

ORD record
ord-820928228203497083b25afe6ba075de
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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