1-Ethenyl-3-methylbenzene → HCID 54230854, compound

HRID 1601030Notes

Reaction equation

HRID 1601030 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([O:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:7]2.[CH:19]([C:21]1[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)=[CH2:20].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCCCCC.CCOC(C)=O>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:23]1([CH3:27])[CH:24]=[CH:25][CH:26]=[C:21]([CH:19]=[CH:20][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][N:6]([O:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:7]3)[CH:22]=1

Participants

7

Reactant 4

HCID 75291-Ethenyl-3-methylbenzeneHCID 80271Tri-o-tolylphosphineHCID 21226206Ethyl acetate hexaneHCID 54306446HCID 54306446, compound

Product 1

HCID 54230854HCID 54230854, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 5-bromo-2-trifluoroacetoxy-1,2,3,4-tetrahydroisoquinoline (616 mg, 2 mmol), 3-vinyltoluene (330 mg, 2.5 mmol), tri-o-tolylphosphine (50 mg) and palladium acetate (20 mg) in triethylamine (1 mL) were heated in a pressure bomb at 100° C. for 8 h. Column chromatography of the dark mixture (silica gel; hexane/EtOAc 40:1 then 20:1) afforded the title compound. FAB ms (m+1) 346.18

Sources & evidence

ORD record
ord-7ae93ee29eb6411287671c0169a760e5
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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