Benzyl Bromide → HCID 19418985, compound

HRID 864368Notes

Reaction equation

HRID 864368 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:1]([N:12]1[CH2:13][CH2:14][C:15](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([F:9])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 19418984HCID 19418984, compound

Product 1

HCID 19418985HCID 19418985, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl bromide (0.45 ml, 3.8 mmol) was added to a solution of (E)-3-fluoro-4-(2-phenylethenyl)pyridine (0.6781 g, 3.40 mmol) in anhydrous dimethylformamide (5 ml) and the mixture stirred at 90° C. under nitrogen for 1 hour. The mixture was allowed to cool and diluted with ethanol (50 ml). Sodium borohydride (0.1580 g, 4.18 mmol) was added portionwise and the resulting reaction mixture stirred at room temperature for 2 hours. The mixture was concentrated in vacuo, water (100 ml) added and extracted with diethyl ether (2×100 ml). The extracts were washed with brine (100 ml), combined, dried (MgSO4) and concentrated in vacuo. Careful purification by first flash chromatography, eluting with ethyl acetate/petrol (60°-80°), followed by preparative layer chromatography, eluting with ethyl acetate/dichloromethane/petrol (60°-80°), gave the title compound (0.1058 g, 11%) as a pale yellow solid; δH (CDCl3) 2.43 (2H, m, tetrahydropyridinyl CH2), 2.69 (2H, m, tetrahydropyridinyl CH2), 3.18 (2H, br s, tetrahydropyridinyl CH2), 3.67 (2H, s, PhCH2N), 6.42 (1H, d, J 16.4Hz, CH=CHPh) and 7.20-7.49 (11H, m, CH=CHPh and ArH).

Workup

  1. temperatureto cool
  2. customthe resulting reaction mixture
  3. stirringstirred at room temperature for 2 hours
  4. concentrationThe mixture was concentrated in vacuo, water (100 ml)
  5. additionadded
  6. extractionextracted with diethyl ether (2×100 ml)
  7. washThe extracts were washed with brine (100 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customCareful purification by first flash chromatography
  11. washeluting with ethyl acetate/petrol (60°-80°)
  12. washeluting with ethyl acetate/dichloromethane/petrol (60°-80°)

Sources & evidence

ORD record
ord-d394b85d9d8d45cba27d9d64f3d263ff
Source dataset
uspto-grants-1996_10
Patent number
US05563150

Reaction notes

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