N-bromobutanimide → Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

HRID 595940Notes

Reaction equation

HRID 595940 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:26])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046154Methyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate

Product 1

HCID 118045477Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate (5.64 g, 22.90 mmol) in acetonitrile (229 mL) was added NBS (4.16 g, 23.36 mmol) in two portions at 0° C. The reaction mixture was stirred at 0° C. for 20 min. After quenched with sat Na2S2O3 and NaHCO3, and stir for 30 min. The reaction mixture was extracted with EtOAc 3 times, the organic washed by sat NaHCO3, water and brine. Dried and concentrated. The crude material was triturated with ether to provide 7.05 g of methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate in 95% yield. LCMS (m/z): 327.1 (MH+), 0.66 min.

Workup

  1. customAfter quenched with sat Na2S2O3 and NaHCO3
  2. stirringstir for 30 min
  3. extractionThe reaction mixture was extracted with EtOAc 3 times
  4. washthe organic washed
  5. customDried
  6. concentrationconcentrated
  7. customThe crude material was triturated with ether

Sources & evidence

ORD record
ord-1970a7aad62d4378b02179655ce94a86
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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