Acetonitrile → HCID 70125162, compound

HRID 1250249Notes

Reaction equation

HRID 1250249 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.[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:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1)[CH3:14]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 15546849N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine

Product 1

HCID 70125162HCID 70125162, compoundYield 111.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
82.5 °C

Procedure

Under a nitrogen atmosphere, a mixture of 4-bromo-1,2-(methylenedioxy)benzene (1.20 g, 5.97 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.19 g, 5.97 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.7 mL, 11.9 mmol) and anhydrous acetonitrile (3.4 mL) was stirred and heated under reflux at 80-85° C. (oil bath temperature) for 22 h. The resulting mixture, containing brown solids, was cooled to ambient temperature, diluted with water (25 mL), and extracted with CHCl3 (3×25 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation and dried under high vacuum to produce an orange-yellow oil (2.13 g). The crude product was purified by column chromatography on silica gel (100 g), eluting with ethyl acetate-hexane (15:85, v/v). Selected fractions containing the product (Rf 0.33) were combined, concentrated by rotary evaporation and the residue was vacuum dried to give 1.08 g (56.6%) of a light-yellow oil.

Workup

  1. temperatureheated
  2. additionThe resulting mixture, containing brown solids
  3. temperaturewas cooled to ambient temperature
  4. extractionextracted with CHCl3 (3×25 mL)
  5. dry with materialThe combined CHCl3 extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-55a7c763e45f4075adbd3eb4099071f5
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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