Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

HRID 641869Notes

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH3:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[N:12]([S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:30])=[O:29])[CH:11]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

NaH (330 mg, 8.25 mmol) was added in several batches, to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (1.4 g, 5.42 mmol) in DMF (25 mL) while cooling to 0-5° C. The resulting solution was stirred at room temperature for 0.5 hours, and then benzenesulfonyl chloride (1.5 g, 8.41 mmol) was added dropwise. The reaction was stirred for an additional 4 hours at room temperature, and then filtered. The filter cake was washed with ethanol (3×50 mL) and dried to afford 1.2 g (55%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1-(phenylsulfonyl)-1H-indole as a light yellow solid. 1H NMR (DMSO) δ 8.62 (s, 1H), 8.17-8.27 (3H), 8.10 (d, 2H), 7.74 (1H), 7.61 (2H), 6.32 (s, 1H), 3.84 (s, 2H), 3.38 (2H), 2.83-2.87 (5H).

Workup

stirringThe reaction was stirred for an additional 4 hours at room temperature
filtrationfiltered
washThe filter cake was washed with ethanol (3×50 mL)
customdried

Sources & evidence

ORD record: ord-7eb0138abb94455d8a85cf588fe857a9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696229B2

Reaction notes

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