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

HRID 340252노트

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HRID 340252 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c70f2e941fc54793b226a74c3d2e68c7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895577B2

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