1-(Benzenesulfonyl)-5-bromo-1H-indole → 1-Benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

HRID 1279384Notes

Reaction equation

HRID 1279384 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][C:35]#[CH:36])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:36]#[C:35][CH2:34][CH2:33][N:30]4[CH2:29][CH2:28][CH:27]([CH2:20][C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:32][CH2:31]4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indoleHCID 106093551-(3-Butynyl)-4-benzylpiperidine

Product 1

HCID 184279561-Benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indoleYield 80.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Procedure

A mixture of 1-benzenesulfonyl-5-bromoindole (1.34 g, 4 mmol), 4-benzyl-1-(3-butynyl)-piperidine (908 mg, 4 mmol) and tetrakis(triphenylphosphine)palladium (0) (600 mg) is stirred in pyrrolidine (50 mL) at 50° C. under N2 overnight. Most of the pyrrolidine is evaporated and the residue purified by medium-pressure column chromatography on silica gel eluting with 50% increasing to 100% EtOAc/hexanes to give the title compound as a pale yellow oil (1.55 g)

Workup

  1. customMost of the pyrrolidine is evaporated
  2. customthe residue purified by medium-pressure column chromatography on silica gel eluting with 50%
  3. temperatureincreasing to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-7997806fe34f44889798bd0d3a89202b
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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