Piconol → HCID 58075191, compound

HRID 868748Notes

Reaction equation

HRID 868748 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1>C1COCC1>[Cl:11][C:12]1[N:13]=[N:14][C:15]([O:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 58075191HCID 58075191, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of NaH (1.44 g, 36 mmol, 60% in mineral oil) in THF (15 mL) was added pyridin-2-ylmethanol (1.16 ml, 12 mmol) and the mixture was stirred for 30 min at rt. Then 3,6-dichloropyridazine (1.79 g, 14 mmol) was added and the mixture was stirred at 55° C. for 4 hours. The reaction was quenched with water and sat. NaHCO3 was added. The product was then extracted with EtOAc, dried over MgSO4 filtered and evaporated. The residue was purified on silica gel(Eluent: 80% EtOAc in hexanes) to give 3-chloro-6-(pyridin-2-ylmethoxy)pyridazine as a white solid (1.64 g, 62%). 1H NMR (300 MHz, dMSO): δ 5.57 (s, 2H), 7.35-7.38 (m, 1H), 7.48-7.54 (m, 2H), 7.82-7.88 (m, 2H), 8.57-8.59 (dd, 1H); MS (M+H, 222).

Workup

  1. stirringthe mixture was stirred at 55° C. for 4 hours
  2. customThe reaction was quenched with water and sat. NaHCO3
  3. additionwas added
  4. extractionThe product was then extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel(Eluent: 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5efe91b4a1324fc7b1c3c9f4be2e82c3
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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