Acetonitrile → HCID 22060164, compound

HRID 1977151Notes

Reaction equation

HRID 1977151 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[N:6][CH:7]=1.[CH3:12][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]([CH2:16][CH:17]=[CH2:18])[CH3:15].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>[CH3:12][N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH:14]([CH2:16]/[CH:17]=[CH:18]/[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[CH:3]=1)[CH3:15]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 105848083-Bromo-5-(propan-2-yloxy)pyridineHCID 15546849N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine

Product 1

HCID 22060164HCID 22060164, compoundYield 119%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, a mixture of 5-bromo-3-isopropoxypyridine (847.0 mg, 3.92 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (784.7 mg, 3.94 mmol), palladium(II) acetate (9.0 mg, 0.04 mmol), tri-o-tolylphosphine (50.0 mg, 0.16 mmol), triethylamine (0.73 g, 7.21 mmol), and anhydrous acetonitrile (2 mL) was stirred and heated under reflux at 80° C. for 20 h. The mixture, containing solids was cooled, diluted with water (10 mL), and extracted with CHCl3 (3×10 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to give an oily residue (1.56 g). The crude product was purified by column chromatography on silica gel, eluting with 25→40% (v/v) ethyl acetate in hexane. Selected fractions containing the product were combined and concentrated to give 1.15 g (87.8%) of a light-amber oil.

Workup

  1. temperatureheated
  2. additionThe mixture, containing solids
  3. temperaturewas cooled
  4. extractionextracted with CHCl3 (3×10 mL)
  5. dry with materialThe combined CHCl3 extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-87db89aa55ca4d7fb4d999dbc2b4d5c6
Source dataset
uspto-grants-2001_05
Patent number
US06232316B1

Reaction notes

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