N-bromobutanimide → 5-Bromo-4-fluoropyridin-2-amine

HRID 595849Notes

Reaction equation

HRID 595849 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(#N)C>[Br:16][C:7]1[C:2]([F:1])=[CH:3][C:4]([NH2:8])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 183278082-Amino-4-fluoropyridine

Product 1

HCID 579174075-Bromo-4-fluoropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-fluoropyridin-2-amine (400 mg, 3.57 mmol) in acetonitrile (35. 7 mL) was added NBS (648 mg, 3.64 mmol) in three portions at 0° C. The reaction mixture was stirred at 0° C. for 20 min. LCMS showed the reaction complete. After quenched with sat Na2S2O3 and NaHCO3, stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times. Washed by sat NaHCO3, water and brine. Dried and concentrated. The crude material was triturated with ether and taken to the next step without further purification. LCMS (m/z): 192.9 (MH+), 0.32 min.

Workup

  1. customthe reaction complete
  2. customAfter quenched with sat Na2S2O3 and NaHCO3
  3. stirringstirred for 30 min
  4. extractionThe reaction mixture was extracted with EtOAc 3 times
  5. washWashed
  6. customDried
  7. concentrationconcentrated
  8. customThe crude material was triturated with ether
  9. customtaken to the next step without further purification
  10. custom192.9 (MH+), 0.32 min.

Sources & evidence

ORD record
ord-b72c715eb5734b23879523d7ca3a1739
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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