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Triethylamine → 3-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole

HRID 342027
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HRID 342027 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH2:28]([Si:30]([C:35]#[CH:36])([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:29].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Cu]I>[N:23]1([CH2:22][CH2:21][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:29]#[C:28][Si:30]([CH2:35][CH3:36])([CH2:33][CH3:34])[CH2:31][CH3:32])[CH:3]=3)[N:7]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 637947(Triethylsilyl)acetyleneHCID 158384865-Bromo-3-(2-pyrrolidinylethyl)-1-(p-toluene-sulfonyl)-indole

생성물 1

HCID 158384873-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole수율 39%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 1140Toluene용매

실험 절차

To a solution of 5-bromo-3-(2-pyrrolidinylethyl)-1-(p-toluenesulfonyl)-indole (Example 5, 415 mg, 1 mmol) in toluene (20 mL), were added triethylsilylacetylene (0.72 mL, 4 mmol, dichlorbis(triphenylphosphine) palladium (II) (210 mg, 0.3 mmol), copper (I) iodide (57 mg, 0.3 mmol) and triethylamine (1 mL). The resulting mixture was stirred under argon at reflux overnight and then evaporated to dryness. Chromatography on silica gel (ethyl acetate followed by methanol) gave the title compound as a yellow oil (197 mg, 39%).

후처리

  1. temperatureat reflux overnight
  2. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b7616756be1a48adaf86d419002a3d66
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05856510

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