Hydrogen Bromide → HCID 58452552, compound

HRID 70614Notes

Reaction equation

HRID 70614 reaction equation
Br.[CH:2]1([CH2:7][CH:8]([C:17]2[N:22]=[C:21]([O:23]C)[C:20]([CH3:25])=[CH:19][CH:18]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:2]1([CH2:7][CH:8]([C:17]2[NH:22][C:21](=[O:23])[C:20]([CH3:25])=[CH:19][CH:18]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 673994926-{2-Cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-2-methoxy-3-methylpyridine

Product 1

HCID 58452552HCID 58452552, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

48% hydrobromic acid (2 mL) was added to a solution of 6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-2-methoxy-3-methylpyridine (220 mg) in acetonitrile (2 mL), and the mixture was stirred at 110° C. for two hours. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=0:1) to give the title compound as a colorless amorphous (200 mg, 94%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=0:1)

Sources & evidence

ORD record
ord-f7ddecf2c4a04ae5b8defba9ce510c2c
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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