Triethylamine → HCID 22060186, compound

HRID 2064300Notes

Reaction equation

HRID 2064300 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:9][CH:10]([OH:14])[CH2:11][CH:12]=[CH2:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[Br:8][C:6]1[CH:7]=[C:2](/[CH:13]=[CH:12]/[CH2:11][CH:10]([OH:14])[CH3:9])[CH:3]=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 122474-Penten-2-OLHCID 693693,5-DibromopyridineHCID 80271Tri-o-tolylphosphine

Product 1

HCID 22060186HCID 22060186, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3,5-dibromopyridine (23.60 g, 100.0 mmol), 4-penten-2-ol (10.8 g, 125.0 mmol), palladium(II) acetate (230 mg, 1.02 mmol), tri-o-tolylphosphine (1.20 g, 3.94 mmol), triethylamine (29.7 mL, 213.45 mmol), and acetonitrile (40 mL) was heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with chloroform (3×200 mL). The combined chloroform extracts were dried over sodium sulfate and filtered. Removal of solvent by rotary evaporation, followed by column chromatography over silica gel eluting with acetone-chloroform (1:9, v/v) furnished 8.10 g (34.0%) of a pale-yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with chloroform (3×200 mL)
  3. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customRemoval of solvent
  6. customby rotary evaporation

Sources & evidence

ORD record
ord-9f6c5932a4514e4c84a7f5dadfa4f5e5
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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