Acetonitrile → HCID 22060191, compound

HRID 1824769Notes

Reaction equation

HRID 1824769 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6](Br)[CH:7]=[N:8][CH:9]=1)[CH3:2].[CH3:11][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]([CH2:15][CH:16]=[CH2:17])[CH3:14].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>[CH3:11][N:12]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH:13]([CH2:15]/[CH:16]=[CH:17]/[C:6]1[CH:7]=[N:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[CH3:14]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 122934803-Bromo-5-ethoxypyridineHCID 15546849N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine

Product 1

HCID 22060191HCID 22060191, compoundYield 88.8%

Reagents, catalysts & solvents 3

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

Procedure

Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80–85° C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3×20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluting with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux at 80–85° C. for 28 h
  3. additionThe resulting mixture, containing beige solids
  4. extractionextracted with CHCl3 (3×20 mL)
  5. dry with materialThe combined light-yellow CHCl3 extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-955d89c329454691b631862d29a041ae
Source dataset
uspto-grants-2006_05
Patent number
US07045538B2

Reaction notes

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