Potassium Carbonate → (5-Bromo-6-fluoro-pyridin-2-yl)-(2-chloro-benzyl)-amine

HRID 1775150Notes

Reaction equation

HRID 1775150 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[N:7]=1.[Br:17]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:17][C:9]1[CH:10]=[CH:11][C:6]([NH:5][CH2:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[Cl:1])=[N:7][C:8]=1[F:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 57963158(2-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

Product 1

HCID 57619357(5-Bromo-6-fluoro-pyridin-2-yl)-(2-chloro-benzyl)-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To (2-chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine (16, 4.70 g, 19.8 mmol) in 100.0 mL of acetonitrile, N-bromosuccinimide (3.53 g, 19.8 mmol) in 20.0 mL of acetonitrile was added slowly at room temperature. The reaction was stirred at room temperature for 4 hours, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate in hexane to provide the desired compound (17, 5.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. washThe resulting material was washed with ethyl acetate in hexane

Sources & evidence

ORD record
ord-2649a3fcb3194c0fb4e4a7db993e28a6
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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