Potassium tert-butoxide → 5-nitro-2-(pyridin-2-yl)-1H-indole

HRID 1403950

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=1)([O-:3])=[O:2].CC([O-])(C)C.[K+]>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:9][CH:10]=1)[NH:8][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:11]2)([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To the solution of 4-nitro-2-(pyridin-2-ylethynyl)aniline (1.5 g, 6.3 mmol) in DMF (50 mL) was added t-BuOK (1.5 g, 13 mmol). The reaction mixture was stirred at 90° C. for 2 h. The mixture was diluted with water and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 5-nitro-2-(pyridin-2-yl)-1H-indole (1.0 g, 67% yield). 1H NMR (300 MHz, d-DMSO) & 12.40 (s, 1H), 8.66 (d, J=2.1 Hz, 1H), 8.58 (d, J=1.8 Hz, 1H), 8.07-7.91 (m, 3H), 7.59 (d, J=6.6 Hz, 1H), 7.42-7.37 (m, 2H).

Workup

extractionextracted with dichloromethane (3×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuum
customThe residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-29aa5492587f4c82b51fb1491a518d2e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912199B2

Linked notes

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