Indole → HCID 57565259, compound

HRID 2110126Notes

Reaction equation

HRID 2110126 reaction equation
N1C2C(=CC=CC=2)C=C1.[F:10][C:11]([F:37])([F:36])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][CH2:31][CH2:30]4)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>ClCCl>[F:36][C:11]([F:10])([F:37])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][N:21]([S:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][CH:31]=[CH:30]4)(=[O:26])=[O:25])[CH2:22][CH2:23]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57565299HCID 57565299, compound

Product 1

HCID 57565259HCID 57565259, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-|4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl|-1H-indole: 5-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-2,3-dihydro-1H-indole (180 mg, 0.44 mmol) was dissolved in dichloromethane (10 mL). DDQ (100 mg, 0.44 mmol) was added and stirred at room temperature for 4 h. The reaction was concentrated and purified by silica gel flash column chromatography (45% ethyl acetate in hexanes) to provide 5-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-1H-indole (70%) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ 11.72 (s, 1H), 8.07(s, 1H) 7.65 (d, 1H), 7.62-7.61 (m, 1H), 7.52-7.48 (m, 3H), 7.04 (d, 2H), 6.71 (m, 1H), 3.40-3.36 (m, 4H), 3.02-2.99 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel flash column chromatography (45% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f874c0c2d724401b90280cf66503331d
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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