1-Ethenyl-3-methylbenzene → HCID 69945928, compound

HRID 724930Notes

Reaction equation

HRID 724930 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[CH2:26].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH:26]=[CH:25][C:24]3[CH:23]=[C:22]([CH3:21])[CH:29]=[CH:28][CH:27]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

Participants

8

Reactant 3

HCID 75291-Ethenyl-3-methylbenzeneHCID 516892Sodium BicarbonateHCID 10547779HCID 10547779, compound

Product 1

HCID 69945928HCID 69945928, compoundYield 87.7%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.15 g, 0.4 mmol), 3-methylstyrene (0.05 mL, 0.4 mmol), palladium acetate (29 mg, 0.13 mmol), sodium bicarbonate (83 mg, 1.0 mmol), tetrabutylammonium chloride (0.11 g, 0.47 mmol), and 1 crystal of BHT in 2 mL of N,N-dimethylformamide was heated at 90° C. under argon for 4.5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated. Purification by flash chromatography, eluting with ethyl acetate/hexanes, afforded 0.13 g of the title compound, m.p. 207°-208° C. (ethyl acetate/hexanes).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customPurification by flash chromatography
  6. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0f3af44016464a439aa6424a5b78f39e
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

Loading…