Sodium Thiosulfate → (5-Bromo-6-fluoro-pyridin-2-yl)-(4-chloro-benzyl)-amine

HRID 1754723Notes

Reaction equation

HRID 1754723 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[Br:17][C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9][C:10]=1[F:14]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 57619459(4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

Product 1

HCID 57619198(5-Bromo-6-fluoro-pyridin-2-yl)-(4-chloro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (4-chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine (536, 1.03 g, 4.35 mmol) in acetonitrile (30.0 mL), under an atmosphere of nitrogen, N-bromosuccinimide (0.820 g, 4.61 mol) was added slowly. After 2 hours, the reaction was poured into a solution of sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and crystallized with ethyl acetate and hexane to give a white solid (537, 1.10 g, 80.1%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customcrystallized with ethyl acetate and hexane
  5. customto give a white solid (537, 1.10 g, 80.1%)

Sources & evidence

ORD record
ord-abe304a3b3f140989f89c4b7d77806c0
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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