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

HRID 342027
Notes
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Reaction equation

HRID 342027 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 1140TolueneSolvent

Procedure

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%).

Workup

  1. temperatureat reflux overnight
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-b7616756be1a48adaf86d419002a3d66
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05856510

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes