3-Bromopyridine → 2,2'-[5-(1-Hydroxy-1-(3-pyridyl]methyl)-1,3-phenylene]di(2-methyl propiononitrile)

HRID 2107772Notes

Reaction equation

HRID 2107772 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH:13]([C:15]1[CH:16]=[C:17]([C:26]([CH3:30])([CH3:29])[C:27]#[N:28])[CH:18]=[C:19]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])[CH:20]=1)=[O:14]>C(OCC)C.CCCCCC>[OH:14][CH:13]([C:15]1[CH:20]=[C:19]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])[CH:18]=[C:17]([C:26]([CH3:30])([CH3:29])[C:27]#[N:28])[CH:16]=1)[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 115069812-[3-(2-Cyanopropan-2-yl)-5-formylphenyl]-2-methylpropanenitrileHCID 178418339Butyllithium

Product 1

HCID 193494362,2'-[5-(1-Hydroxy-1-(3-pyridyl]methyl)-1,3-phenylene]di(2-methyl propiononitrile)

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of 3-bromopyridine (0.31 g) in diethyl ether was stirred and cooled to -70° while a solution of n-butyl-lithium in hexane (1.6M, 1.33 ml) was added, followed by 2,2'-(5 formyl-1,3-phenylene)di(2-methylpropiononitrile), (0.48 g). The mixture was allowed to warm to room temperature and was then extracted with 2N aqueous hydrochloric acid (10 ml). The acid extract was separated, basified with 10N aqueous sodium hydroxide solution and extracted twice with ethyl acetate. The extracts were combined, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography, eluting with ethyl acetate, to give 2,2'-[5-(1-hydroxy-1-(3-pyridyl]methyl)-1,3-phenylene]di(2-methyl propiononitrile), mp. 117°-120°.

Workup

  1. additionwas added
  2. extractionwas then extracted with 2N aqueous hydrochloric acid (10 ml)
  3. extractionThe acid extract
  4. customwas separated
  5. extractionextracted twice with ethyl acetate
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customthe residue was purified by flash column chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-44e607727bb842f0ad08138f3c916d50
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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