Acetonitrile → HCID 22060168, compound

HRID 1828939Notes

Reaction equation

HRID 1828939 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[N:6][CH:7]=1.[CH3:10][CH:11]([OH:15])[CH2:12][CH:13]=[CH2:14].C(N(CC)CC)C.C(#N)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:9][O:8][C:4]1[CH:3]=[C:2](/[CH:14]=[CH:13]/[CH2:12][CH:11]([OH:15])[CH3:10])[CH:7]=[N:6][CH:5]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 122474-Penten-2-OLHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 22060168HCID 22060168, compoundYield 83.6%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-bromo-3-methoxypyridine (4.11 g, 21.86 mmol), 4-penten-2-ol (2.25 g, 26.23 mmol), palladium(II) acetate (49 mg, 0.22 mmol), tri-o-tolylphosphine (266 mg, 0.87 mmol), triethylamine (13.71 mL, 98.37 mmol), and acetonitrile (15 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, filtered, and concentrated by rotary evaporation to give 3.53 g (70.3%) 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. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-20683bd3183f44eb949842bdb99547fe
Source dataset
uspto-grants-2006_06
Patent number
US07060826B2

Reaction notes

Loading…