5-Nitroindole → 5-Nitro-1-tetrahydropyran-2-ylindole

HRID 1418031Notes

Reaction equation

[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-:5])=[O:4].[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1Cl>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1)[CH:10]=[CH:9]2)([O-:5])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

6.3 g of 55% NaH are added, at 0° C., under an argon atmosphere, to 20 g of 5-nitroindole in solution in 200 ml of dimethylformamide. After stirring for 15 minutes at 0° C., 27.1 g of tetrahydropyranyl chloride are added to the reaction mixture. After stirring for 24 hours at room temperature, the reaction mixture is poured onto 1200 ml of ice-cold water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a column of silica gel eluted with a 4/1 (v/v) cyclohexane/ethyl acetate mixture, to provide 19 g of 5-nitro-1-tetrahydropyran-2-ylindole. 1H NMR (DMSO): 1.34-2.12 (m, 6H), 3.67-4.48 (m, 2H), 5.70 (dd, J=2.0, 10.2, 1H), 6.75 (d, J=3.4, 1H), 7.72-7.76 (m, 2H), 8.02 (dd, J=2.2, 9.2, 1H), 8.54 (d, J=2.2, 1H).

Workup

stirringAfter stirring for 24 hours at room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulphate
customevaporated to dryness
customThe residue is purified by chromatography on a column of silica gel
washeluted with a 4/1 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record: ord-63aae832a2424cddacf76fca2ff3e84d
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880135

Reaction notes

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