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

HRID 1755299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755299
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-687e63ca44b540acb801f50735657ab3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169259B2

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