Benzyl Bromide → HCID 23502804, compound

HRID 1835372Notes

Reaction equation

HRID 1835372 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([OH:22])=[N:11][CH:10]=1.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl.C(=O)([O-])[O-].[Ag+2]>[CH2:34]([O:22][C:12]1[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:9]([C:8]([N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:32])([F:1])[F:33])[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=2)[CH3:24])=[O:23])=[CH:10][N:11]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178424180HCID 178424180, compound

Product 1

HCID 23502804HCID 23502804, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 50 mg (0.11 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-hydroxy-N-methyl-4-o-tolyl-nicotinamide (Example 111), 0.014 ml (0.12 mmol) benzyl bromide and 59 mg (0.21 mmol) silver carbonate in 2 ml dichloromethane was heated at reflux for 2 h. Cooling to room temperature was followed by dilution with dichloromethane and filtration. The filtrate was washed with water. The aqueous layer was extracted with three portions of dichloromethane. The combined organic layers were dried with sodium sulfate, concentrated and dried in high vacuo. Column chromatography afforded 24 mg (41%) of the title compound as a viscous light yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationwas followed by dilution with dichloromethane and filtration
  4. washThe filtrate was washed with water
  5. extractionThe aqueous layer was extracted with three portions of dichloromethane
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. concentrationconcentrated
  8. customdried in high vacuo

Sources & evidence

ORD record
ord-70ac7d88daad423d87be8e226618d2ac
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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