4-[2-(2-Fluorophenyl)ethyl]-3-methoxypyridine → HCID 22248091, compound

HRID 890065Notes

Reaction equation

HRID 890065 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[O:16][CH3:17]>C(#N)C.C(Br)C1C=CC=CC=1>[CH2:8]([N:13]1[CH2:14][CH2:15][C:10]([CH2:9][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([O:16][CH3:17])[CH2:12]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

4

Reactant 1

HCID 222482284-[2-(2-Fluorophenyl)ethyl]-3-methoxypyridine

Product 1

HCID 22248091HCID 22248091, compoundYield 159.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 7498Benzyl BromideSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving 1.12 g of 4-[2-(2-fluorophenyl)ethyl]-3-methoxypyridine in 10 ml of acetonitrile, 0.63 ml of benzyl bromide was added, the mixture was stirred for 2 hours at 50° C., and the solvent was distilled off under reduced pressure. The residue was dissolved in 20 ml of methanol, and then 552 mg of sodium borohydride was added while cooling on ice and the mixture was stirred for 1 hour. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered with NH silica gel. The solvent was distilled off under reduced pressure to obtain the title compound (1.26 g, 80% yield).

Workup

  1. additionwas added
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 20 ml of methanol
  4. addition552 mg of sodium borohydride was added
  5. temperaturewhile cooling on ice
  6. stirringthe mixture was stirred for 1 hour
  7. additionWater was added to the reaction solution, and extraction
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered with NH silica gel
  11. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cee0d3c794cb4e1499e14d7b28062364
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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