Ethanol → HCID 58755934, compound

HRID 1625572Notes

Reaction equation

HRID 1625572 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:7]=1.CCO.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=1[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 58075191HCID 58075191, compound

Product 1

HCID 58755934HCID 58755934, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3-Chloro-6-(pyridin-2-ylmethoxy)pyridazine (Example 15a) (221 mg, 1 mmol) was dissolved in toluene (10 mL), EtOH (2 mL), and water (1.5 mL). Then 2,4-dimethylphenylboronic acid (150 mg, 1 mmol) was added, followed by K2CO3 (276 mg, 2 mmol) and the mixture was degassed using argon stream. Tetrakis(triphenylphosphine)palladium (232 mg, 0.2 mmol) was added under argon and the mixture was refluxed overnight. The solvents were removed under vacuum and a residual solid was extracted with EtOAc, and successively washed with water and brine dried over MgSO4 filtered and evaporated. The crude material was purified on silica gel (Eluent: 50% EtOAc in hexanes) to give 3-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethoxy)pyridazine (169 mg, 58%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.26 (s, 3H), 2.32 (s, 3H), 5.62 (s, 2H), 7.13-7.15 (m, 2H), 7.28-7.40 (m, 2H), 7.55-7.56 (d, 1H), 7.78-7.84 (m, 2H), 8.58-8.60 (d, 1H); MS (M+H, 292).

Workup

  1. customthe mixture was degassed
  2. temperaturethe mixture was refluxed overnight
  3. customThe solvents were removed under vacuum
  4. extractiona residual solid was extracted with EtOAc
  5. washsuccessively washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude material was purified on silica gel (Eluent: 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0db18503de774fa9be0645fafaa28cd4
Source dataset
uspto-grants-2014_07
Patent number
US08784782B2

Reaction notes

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