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

HRID 366518Notes

Reaction equation

HRID 366518 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[C:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH:26]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:25][CH2:24]4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.C1(S(N2C3C(=CC(Br)=CC=3)C=C2)(=O)=O)C=CC=CC=1.C(C1CCN(CCC#C)CC1)C1C=CC=CC=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>[CH2:29]([CH:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][C:20]#[C:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[NH:10][CH:11]=[CH:12]3)[CH2:24][CH2:25]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indoleHCID 106093551-(3-Butynyl)-4-benzylpiperidineHCID 184279561-Benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

Product 1

HCID 106410735-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Procedure

1-Benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole. 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-faa41fc2b5794bc9abffe270128afd8d
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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