Bromine → Methyl 4-(6-amino-5-bromopyridazin-3-yl)benzoate

HRID 1755312Notes

Reaction equation

HRID 1755312 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[Br:23]Br>CO>[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[Br:23]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 86682704Methyl 4-(6-aminopyridazin-3-yl)benzoate

Product 1

HCID 86682705Methyl 4-(6-amino-5-bromopyridazin-3-yl)benzoateYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 mL round bottom flask was placed methyl 4-(6-aminopyridazin-3-yl)benzoate (2.8 g, 12.2 mmol), NaHCO3 (2.05 g, 22.4 mmol) and methanol (100 mL) and to this suspension was added Br2 (1.95 g, 12.2 mmol) drop wise over about 30 minutes at room temperature. The mixture was stirred for 16 h, then filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=2:1) to give methyl 4-(6-amino-5-bromopyridazin-3-yl)benzoate (1.64 g, 43.6%) as a light orange solid. LC-MS: [M+H]+, 309.9, tR=1.397 min.

Workup

  1. customIn a 250 mL round bottom flask was placed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7fcaa08492df47a086575e9da87316fc
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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