N-bromobutanimide → Methyl 4-(3-amino-6-bromopyrazin-2-yl)-2-fluorobenzoate

HRID 595989Notes

Reaction equation

HRID 595989 reaction equation
[NH2:1][C:2]1[C:3]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:26])C(=O)C1.C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:1][C:2]1[C:3]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[N:4][C:5]([Br:26])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 118045820Methyl 4-(3-aminopyrazin-2-yl)-2-fluorobenzoate

Product 1

HCID 118046172Methyl 4-(3-amino-6-bromopyrazin-2-yl)-2-fluorobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of methyl 4-(3-aminopyrazin-2-yl)-2-fluorobenzoate (31.5 g, 127 mmol) in acetonitrile (430 mL) at 0° C. was added NBS (23.9 g, 134 mmol). The reaction mixture was stirred in ice bath for 1 h, sat. sodium bicarbonate was added, stirred 30 min and product was extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was recrystallized in EtOAc and heptane to give methyl 4-(3-amino-6-bromopyrazin-2-yl)-2-fluorobenzoate as brown color solid in 96% yield. LCMS (m/z): 326.0/328.0 (MH+), 0.87 min.

Workup

  1. stirringstirred 30 min
  2. extractionproduct was extracted with ethylacetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was recrystallized in EtOAc

Sources & evidence

ORD record
ord-6cc97469cd2f4be0bc9977d100da46bb
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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