2,6-Di-tert-butyl-4-methylphenol → HCID 12137491, compound

HRID 985366Notes

Reaction equation

HRID 985366 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.[C:20]([C:24]1[CH:29]=[C:28](C)[CH:27]=[C:26](C(C)(C)C)[C:25]=1O)(C)(C)[CH3:21].C([Sn](CCCC)(CCCC)C#CC1C=CC=CC=1)CCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([C:21]#[C:20][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=[C:4]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 630640Tributyl(2-phenylethynyl)stannaneHCID 12137490HCID 12137490, compound

Product 1

HCID 12137491HCID 12137491, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-4-methyl-6-(1-methyl-3-trifluoromethyl-pyrazol-5-yloxy)pyridine (3.0 g, 7.1 mmol), tetrakistriphenyl-phosphine palladium (0.2 g, 1.8 mmol) and 2,6-di-tert-butyl-4-methylphenol (3 crystals) in toluene (40 ml) under a nitrogen atmosphere is added dropwise tributyl-phenylethynyl-stannane (2.9 ml, 7.8 mmol) and the resulting mixture is heated at reflux for 2 hours. After cooling, the reaction mixture is diluted with ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate and dried. 43% of the product (1.1 g, mp. 56° C.) is obtained by flash chromatography.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. customdried

Sources & evidence

ORD record
ord-d642bedc0a12424eac0f59363d6ea1ae
Source dataset
uspto-grants-2005_03
Patent number
US06872690B2

Reaction notes

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