Triethylamine → HCID 23498862, compound

HRID 1836918Notes

Reaction equation

HRID 1836918 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.Br[C:13]1[C:22]([CH2:23][N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:21][C:20]2[C:19]([CH3:30])([CH3:29])[CH2:18][CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=2[CH:14]=1.COC([SiH3])=C(OC)OC.C(N(CC)CC)C>CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([C:13]1[C:22]([CH2:23][N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:21][C:20]2[C:19]([CH3:30])([CH3:29])[CH2:18][CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=2[CH:14]=1)=[CH2:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23498930HCID 23498930, compoundHCID 91996421HCID 91996421, compound

Product 1

HCID 23498862HCID 23498862, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2.076 g (3.99 mmol) 2-bromo-5,5,8,8,-tetramethyl-3-((pyrazol-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene p-toluenesulfonate, 0.045 g (0.20 mmol) of palladium acetate, 0.122 g (0.40 mmol) of tri-o-tolulylphosphine) and 1.22 ml (7.97 mmol) trimethoxyvinylsilane in 8 ml N-methylpyrrolidinone was added 1.80 ml (12.90 mmol) triethylamine. The reaction vessel was evacuated and filled with nitrogen three times then heated to 90° C. for 1.5 hours. The reaction was cooled and stirred for 17 hours at room temperature. The resulting suspension was quenched with 1M hydrochloric acid and extracted with ethyl ether. The organic layer was washed with 1M HCl, water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution with 20% ethyl acetate/hexane) to yield 0.249 g (21%) of 2-vinyl-5,5,8,8,-tetramethyl-3-((pyrazol-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene (M+1=295).

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with nitrogen three times
  3. temperatureThe reaction was cooled
  4. customThe resulting suspension was quenched with 1M hydrochloric acid
  5. extractionextracted with ethyl ether
  6. washThe organic layer was washed with 1M HCl, water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (elution with 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f06c1f2e40d4d0485bbbc5abe35169f
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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