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

HRID 509943Notes

Reaction equation

HRID 509943 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 (45, 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 (46, 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-f1d71c260e0d45758a7d7725d8c48425
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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