3-Bromopyridine → HCID 14989408, compound

HRID 465989Notes

Reaction equation

HRID 465989 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])#[N:14]>CCCCCC.C1COCC1.C(OCC)C>[C:13]([C:15]1[CH:16]=[C:17]([CH:18]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[OH:19])[CH:20]=[CH:21][CH:22]=1)#[N:14]

Participants

7

Reactant 3

HCID 122863-BromopyridineHCID 90670m-FormylbenzonitrileHCID 178418339Butyllithium

Product 1

HCID 14989408HCID 14989408, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

52.8 ml of 2.5 molar butyllithium solution (0.132 mol) in n-hexane are cooled to -78° C. under argon in a mixture of 66 ml of abs. THF and 66 ml of abs. diethyl ether. 17.38 g (0.11 mol) of 3-bromopyridine in 132 ml of abs. diethyl ether are added dropwise to this in the course of 90 min. and the mixture is subsequently stirred for 10 min. 14.5 g (0.11 mol) of 3-cyanobenzaldehyde in 275 ml of abs. diethyl ether and 44 ml of abs. THF are added dropwise to this solution. It is slowly allowed to come to room temperature and stirred overnight at room temperature. It is then stirred into 1100 ml of ice water, extracted twice using 550 ether each time and the combined organic phases are washed by shaking with satd. NaCl solution. After drying over Na2SO4, the organic phase is evaporated and the residue is dried in a high vacuum.

Workup

  1. customto come to room temperature
  2. stirringstirred overnight at room temperature
  3. extractionextracted twice
  4. washthe combined organic phases are washed
  5. stirringby shaking with satd
  6. dry with materialAfter drying over Na2SO4
  7. customthe organic phase is evaporated
  8. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-18949ab090a4424a8548a64ad79ea729
Source dataset
uspto-grants-1992_10
Patent number
US05155121

Reaction notes

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