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

HRID 1755299Notes

Reaction equation

HRID 1755299 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[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:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[Br:23]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 86682701Methyl 3-(6-aminopyridazin-3-yl)benzoate

Product 1

HCID 86682702Methyl 3-(6-amino-5-bromopyridazin-3-yl)benzoateYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 150 mL round bottom flask was placed methyl 3-(6-aminopyridazin-3-yl)benzoate (2.29 g, 10 mmol), NaHCO3 (1.68 g, 20 mmol) and methanol (40 mL). To this suspension was added Br2 (1.6 g, 10 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 3-(6-amino-5-bromopyridazin-3-yl)benzoate (1.2 g, 39%) as a light orange solid. LC-MS: [M+H]+, 308.0, tR=1.377 min.

Workup

  1. customIn a 150 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-687e63ca44b540acb801f50735657ab3
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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