3-Bromo-5-fluoro-4-methylpyridine → HCID 71743410, compound

HRID 717545Notes

Reaction equation

HRID 717545 reaction equation
[Cu]([C:4]#[N:5])C#N.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([F:14])[C:12]=1[CH3:13]>CN(C)C=O>[F:14][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([C:12]=1[CH3:13])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 666852633-Bromo-5-fluoro-4-methylpyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 71743410HCID 71743410, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Copper cyanide (1.87 g, 0.021 mol) was added at room temperature to a sealed tube containing a solution of 3-bromo-5-fluoro-4-methylpyridine (E; 2.0 g, 0.0105 mol) in dimethylformamide (20 mL). The reaction mixture was heated to 150° C. for 16 h. It was then cooled to RT, quenched with 20% aqueous ammonia (30 mL) solution and stirred for 5 min. The reaction mixture was extracted with diethyl ether (2×100 mL). The organic layers were washed with water (2×50 mL), dried over anhydrous sodium sulphate and concentrated to afford 5-fluoro-4-methylnicotinonitrile. 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.56 (s, 1H), 2.56 (s, 3H).

Workup

  1. temperatureIt was then cooled to RT
  2. customquenched with 20% aqueous ammonia (30 mL) solution
  3. extractionThe reaction mixture was extracted with diethyl ether (2×100 mL)
  4. washThe organic layers were washed with water (2×50 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51318b2289cf476984e3606e15ae6d21
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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