Triethylamine → 5-[(Triethylsilyl)ethynyl]-1H-indole

HRID 340252ノート

反応式

HRID 340252 の反応式
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]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 637947(Triethylsilyl)acetyleneHCID 21086119iodo-1H-indole

生成物 1

HCID 668932335-[(Triethylsilyl)ethynyl]-1H-indole

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  1. customVacuumed and nitrogen flushed for three times
  2. customThe vial was sealed
  3. customUpon completion of the reaction
  4. washColumn was washed with hexanes and diethylether until all eluents
  5. additioncontaining product
  6. customwere collected
  7. distillationCarefully distill off
  8. customhexanes and ether using rotary evaporator with minim
  9. temperatureheating

出典と根拠

ORDレコード
ord-c70f2e941fc54793b226a74c3d2e68c7
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

反応ノート

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