Benzene, 1-bromo-3-nitro- → 2-[3-(3-Nitrophenyl)prop-2-ynyl]-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)[C:2]#[CH:3].Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1>C(N(CC)CC)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:21]([C:17]1[CH:16]=[C:15]([C:3]#[C:2][CH2:1][N:4]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)[CH:20]=[CH:19][CH:18]=1)([O-:23])=[O:22]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 81 (2.06 g, 10.2 mmol) in anhydrous triethylamine (30 mL) were sequentially added 1-bromo-3-nitrobenzene (1.83 g, 10.67 mmol), CuI (0.39 g, 2.05 mmol) and Pd(PPh3)4 (1.17 g, 1.0 mmol). The mixture was heated at 90° C. for 1 hour before it was filtered through Celite® and the filtrate was diluted with EtOAc (150 mL). The resulting solution was washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified via flash silica gel chromatography to provide 93 (1.97 g, 66%).
Workup
- filtrationwas filtered through Celite®
- additionthe filtrate was diluted with EtOAc (150 mL)
- washThe resulting solution was washed with water (100 mL), brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified via flash silica gel chromatography
Sources & evidence
- ORD record
- ord-7263c587ce444de1ae78eb86f7fdb86f
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265122B2
Reaction notes
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