Ethyl bromopyruvate → Ethyl 8-bromo-6-chloroimidazo[1,2-b]pyridazine-2-carboxylate

HRID 718565Notes

Reaction equation

HRID 718565 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:9])[N:5]=[N:6][C:7]=1[NH2:8].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[Br:1][C:2]1[C:7]2[N:6]([CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]=2)[N:5]=[C:4]([Cl:9])[CH:3]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 220244193-Amino-4-bromo-6-chloropyridazine

Product 1

HCID 91756831Ethyl 8-bromo-6-chloroimidazo[1,2-b]pyridazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-bromo-3-chloro-6-aminopyridazine (15.7 g, 75.3 mmol) in dry DMF (80 mL) was added ethyl bromopyruvate (21.0 mL, 151 mmol) via a syringe. The resulting mixture was stirred at rt for 20 h. The reaction mixture was poured into ice water (300 mL), and the precipitated solid was isolated by filtration, and washed with water (2×50 mL) and Et2O (3×50 mL). The residual solvents in the solid were removed under reduced pressure to give compound 5a as an off-white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.50 (s, 1H), 7.47 (s, 1H), 4.49 (q, J=7.1 Hz, 2H), 1.44 (t, J=7.1 Hz, 3H).

Workup

  1. customthe precipitated solid was isolated by filtration
  2. washwashed with water (2×50 mL) and Et2O (3×50 mL)
  3. customThe residual solvents in the solid were removed under reduced pressure

Sources & evidence

ORD record
ord-698d09333c5244fa97e2e2d191aa1e06
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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