Styrene → HCID 54195829, compound

HRID 1067297Notes

Reaction equation

HRID 1067297 reaction equation
Br[C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:8][CH2:7]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[CH2:62]=[CH:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH:62]([C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:29])([F:31])[F:30])[CH:21]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:14])([F:15])[F:16])[CH2:8][CH2:7]2)=[CH:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 21192934HCID 21192934, compound

Product 1

HCID 54195829HCID 54195829, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(8-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.525 g), palladium diacetate (0.011 g), tris(o-tolyl)phosphine (0.03 g), triethylamine (0.15 g) and styrene (0.16 g) were combined in acetonitrile and warmed to reflux for 23 h. The mixture was cooled, partitioned between dichloromethane/water, the organic phase separated and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, ethyl acetate/hexane mixtures as eluant) to provide the title compound (0.46 g).

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 23 h
  3. temperatureThe mixture was cooled
  4. custompartitioned between dichloromethane/water
  5. customthe organic phase separated
  6. customsolvent removed at reduced pressure
  7. customchromatographed (silica gel, ethyl acetate/hexane mixtures as eluant)

Sources & evidence

ORD record
ord-b32c68daa3a547dea2b3a189d915ac6f
Source dataset
uspto-grants-2001_06
Patent number
US06248754B1

Reaction notes

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