Triethylamine → 5-[(Triethylsilyl)ethynyl]-1H-indole
Reaction equation
I[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH2:11]([Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:14]#[CH:15])[CH3:12].C(N(CC)CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH2:14]([Si:13]([C:11]#[C:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:2][CH:3]=[CH:4]2)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a scintillation vial was added -iodo-1H-indole (1.1 eq.), triethyl(ethynyl)silane (1 eq.), triethylamine (5 eq.), and anhydrous DMF (0.2 M). Vacuumed and nitrogen flushed for three times. CuI (0.1 eq.) and bis(triphenylphosphine)dichloro-palladium(II) (0.1 eq) were added. The vial was sealed and heated at 60° C. overnight. Upon completion of the reaction as monitored by TLC, the content of the vial was loaded onto a silica gel column pretreated with hexanes. Column was washed with hexanes and diethylether until all eluents containing product were collected. Carefully distill off hexanes and ether using rotary evaporator with minim heating afforded product 5-((triethylsilyl)ethynyl)-1H-indole as colorless oil, which was carried directly on to the next step.
Workup
- customVacuumed and nitrogen flushed for three times
- customThe vial was sealed
- customUpon completion of the reaction
- washColumn was washed with hexanes and diethylether until all eluents
- additioncontaining product
- customwere collected
- distillationCarefully distill off
- customhexanes and ether using rotary evaporator with minim
- temperatureheating
Sources & evidence
- ORD record
- ord-c70f2e941fc54793b226a74c3d2e68c7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895577B2
Reaction notes
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