Imidazole → 3-Chloro-6-(1H-imidazol-1-yl)pyridazine

HRID 253184Notes

Reaction equation

HRID 253184 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.C(N(C(C)C)CC)(C)C>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 673313,6-DichloropyridazineHCID 81531Diisopropylethylamine

Product 1

HCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazineYield 38%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 3,6-dichloropyridazine (Aldrich, 300 mg, 2.0 mmol), imidazole (Aldrich, 163 mg, 2.4 mmol), and diisopropylethylamine (620 mg, 4.8 mmol) in 1.5 mL 1,2-dichlorobenzene was heated in a sealed tube to 120° C. at 330 watts for 45 min in an Emry™ Creator microwave. The crude reaction mixture was purified by column chromatography (SiO2, 1% methanol-CH2Cl2) to give 135 mg of the title compound (0.75 mmol, 38% yield) as the major product. MS (DCl/NH3) m/z 181 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by column chromatography (SiO2, 1% methanol-CH2Cl2)

Sources & evidence

ORD record
ord-2529d6304e2f446c96f5317e1d234d4f
Source dataset
uspto-grants-2011_01
Patent number
US07872010B2

Reaction notes

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