Sodium hydride → HCID 68014853, compound

HRID 1747816Notes

Reaction equation

HRID 1747816 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.[H-].[Na+].Br[CH2:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:29][CH:30]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:27]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][N:7]2[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:20])[C:5]([C:9]3[N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:12]=[CH:11][CH:10]=3)=[N:6]2)[CH:26]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 38644053-(Bromomethyl)biphenylHCID 178493808HCID 178493808, compound

Product 1

HCID 68014853HCID 68014853, compoundYield 49.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (0.0478 g) was dissolved in DMF (3.6 mL), NaH (0.0078 g, 60%, in oil) and tetrabutylammoniumiodide (0.0131 g) were added at 0° C., and the mixture was stirred at the same temperature for 20 min. To the reaction mixture was added 3-(bromomethyl)biphenyl (0.0462 g) at 0° C., and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (0.0385 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2.5 days
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)

Sources & evidence

ORD record
ord-366a0f9813e8447da3ee85ad43891989
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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