Triethylamine → 3-bromo-4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one

HRID 425745Notes

Reaction equation

HRID 425745 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH:17]([F:19])[F:18])[C:10]2[CH2:14][O:13][C:12](=[O:15])[CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:27]N1C(=O)CCC1=O>C(#N)C>[Br:27][C:11]1[C:12](=[O:15])[O:13][CH2:14][C:10]=1[N:9]([CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:16][CH:17]([F:19])[F:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 16752772Flupyradifurone

Product 1

HCID 579083923-bromo-4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-oneYield 78.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

313 mg (1.08 mmol) of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one (1) are dissolved in 20 ml of acetonitrile, and 166 μl (1.19 mmol) of triethylamine and 386 mg (2.17 mmol) of N-bromosuccinimide are added at room temperature. After 3 hours of stirring, the mixture is concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 312 mg (63% of theory) of 3-bromo-4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customPurification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-802accc7a652490cb351286a74d1917a
Source dataset
uspto-grants-2012_01
Patent number
US08106211B2

Reaction notes

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