p-Toluenesulfonic acid → HCID 24743833, compound

HRID 641874Notes

Reaction equation

[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH3:9][N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([NH2:25])=[CH:22][CH:23]=3)[N:18]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:17]=2)[CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:25]([C:21]2[CH:20]=[C:19]3[C:24]([C:16]([C:13]4[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH:12]=4)=[CH:17][N:18]3[S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])=[CH:23][CH:22]=2)[C:5]([CH3:6])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Hexane-2,5-dione (930 mg, 8.16 mmol) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indol-6-amine (1.66 g, 1.13 mmol) in toluene (80 mL). Para-toluenesulfonic acid (30 mg, 0.17 mmol) was then added, and the resulting solution was stirred for 4 hours at 130° C. After filtration, the filtrate was concentrated and the residue was purified by column chromatography using a 30:1 dichloromethane/methanol solvent system. The product was washed with petroleum ether to afford 170 mg (32%) of 6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indole as a yellow solid. 1H NMR (DMSO) δ 8.3 (s, 1H), 8.3 (s, 1H), 8.1 (s, 1H), 8.0 (s, 1H), 7.8 (s, 1H), 7.6 (s, 1H), 7.4 (s, 1H), 7.4 (s, 1H), 7.1 (s, 1H), 6.3 (s, 1H), 5.8 (s, 1H), 5.8 (s, 1H), 3.0 (s, 2H), 2.27 (s, 3H), 2.6 (d, 2H), 2.6 (d, 2H), 1.8 (d, 3H), 1.8 (d, 3H). LC/MS (EI) tR 2.48, m/z 446.0 (M++1)

Workup

filtrationAfter filtration
concentrationthe filtrate was concentrated
customthe residue was purified by column chromatography
washThe product was washed with petroleum ether

Sources & evidence

ORD record: ord-e0c0b9f1b2644d569861924079f2af94
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696229B2

Reaction notes

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