Potassium Carbonate → HCID 18994139, compound

HRID 375060Notes

Reaction equation

HRID 375060 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([CH3:12])[O:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][N:6]=1.Cl[C:16]1[N:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOCCOC.O>[CH3:23][O:22][C:20]1[CH:21]=[C:16]([O:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([O:4][CH:3]([CH3:12])[C:2]([F:1])([F:13])[F:14])[CH:10]=2)[N:17]=[N:18][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109756123-Chloro-5-methoxypyridazineHCID 178467029HCID 178467029, compound

Product 1

HCID 18994139HCID 18994139, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

2-(2,2,2-Trifluoro-1-methylethoxy)-4-pyridinol (0.64 g, 3.09 mmol), 3-chloro-5-methoxy-pyridazine (0.44 g, 3.09 mmol), potassium carbonate (0.85 g, 6.18 mmol) and CuBr (0.89 g, 6.18 mmol) were stirred under nitrogen in diglyme (5 mL) at 100° C. for 6 days. The mixture was then poured in water and extracted several times with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and evaporated in-vacuo. The crude product was purified by flash chromatography to give 5-methoxy-3-[[2-(2,2,2-trifluoro-1-methylethoxy)-4-pyridinyl]oxy]pyridazine (0.42 g, 43% yield, Compound No. 10) as a white solid, mp=100° C. -102° C.

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in-vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b5f0dd7e726b46cdb756714e6f51df0d
Source dataset
uspto-grants-1996_01
Patent number
US05484761

Reaction notes

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