Benzyl Bromide → 2-[(1-Benzyl-3-bromo-pyridin-1-ium-4-yl)methyl]-6-methoxy-tetralin-1-one bromide

HRID 2207207Notes

Reaction equation

HRID 2207207 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[Br-:1].[CH2:22]([N+:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]2=[O:21])=[C:2]([Br:1])[CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 1185580372-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

Product 1

HCID 1185579692-[(1-Benzyl-3-bromo-pyridin-1-ium-4-yl)methyl]-6-methoxy-tetralin-1-one bromideYield 158.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 99 (69.2 mg, 0.2 mmol) was dissolved in dichloromethane (2 mL). Benzyl bromide (48 μL, 0.4 mmol) was then added and the solution was heated under reflux for 12 h in a sealed tube. After concentration under reduced pressure, the solid was triturated with diethylether, filtered and washed (3×) with n-pentane to afford the title product 117 as a pale brown powder (Yield 82 mg, 80%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 12 h in a sealed tube
  3. concentrationAfter concentration under reduced pressure
  4. customthe solid was triturated with diethylether
  5. filtrationfiltered
  6. washwashed (3×) with n-pentane

Sources & evidence

ORD record
ord-77f8d46c7d7f47f8a1d2fa29f220fb71
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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