Water → 3,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine

HRID 429742Notes

Reaction equation

HRID 429742 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[N:10][C:9]=1[Cl:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:15][C:9]1[N:10]=[N:11][C:12]([Cl:14])=[CH:13][C:8]=1[N:1]1[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 127501,2,3,6-TetrahydropyridineHCID 220306484-Bromo-3,6-dichloropyridazine

Product 1

HCID 183533373,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2,3,6-Tetrahydropyridine, (1.04 ml) was added to a stirred solution/suspension of 4-bromo-3,6-dichloropyridazine (2.0 g, 8.8 mmol) and potassium carbonate (2.4 g) in dry DMF (10 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 5 hours. The reaction was poured into water (100 ml) and extracted with ethyl acetate (×3). The combined extracts were washed with water (200 ml), brine, dried (MgSO4), filtered and evaporated. The residue was triturated with ether/petroleum ether to afford a white powder (1.96 g, 97%). 1H NMR (250 MHz, CDCl3) 6.82 (1H, s), 5.97 (1H, m), 5.80 (1H, m), 3.77 (2H, m), 3.59 (2H, m), 2.38 (2H, m). MS (ES+) 232 [MH]+.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined extracts were washed with water (200 ml), brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with ether/petroleum ether

Sources & evidence

ORD record
ord-cc21a2d0d7f540feaca3d85f7bf86317
Source dataset
uspto-grants-2001_11
Patent number
US06319924B1

Reaction notes

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