Hydrogen Peroxide → 8-Fluoro-1-[(2,4,6-trifluorophenyl)amino]-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1971025Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:25]#[N:26])=[CH:12][N:13]=[C:14]([NH:15][C:16]4[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=4[F:24])[C:5]=3[C:4]=2[CH:3]=1.C([O-])([O-])=[O:28].[K+].[K+].OO>CS(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:25]([NH2:26])=[O:28])=[CH:12][N:13]=[C:14]([NH:15][C:16]4[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=4[F:24])[C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

8-Fluoro-1-[(2,4,6-trifluorophenyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile (46.5 mg, 0.13 mmol) and K2CO3 (108 mg, 0.78 mmol) was dissolved in DMSO (2.6 ml). Hydrogen peroxide (30%, 0.100 ml, 1.04 mmol) was added and the solution was heated at 70° C. for three hours. HPLC/MS then showed complete conversion. The solution was cooled to ambient temperature and directly purified by reverse phase HPLC. Desired fractions were combined, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate solution: The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR (600 MHz, CD30OD) δ 8.37 (s, 1H); 8.16 (dd, 1H); 7.64 (dd, 1H); 7.21 (dt, 1H); 6.98 (dd, 2H). LRMS (APCI) calc'd for (C18H10F4N4O) [M+H]+, 375.1. found 375.0.

Workup

temperatureThe solution was cooled to ambient temperature
customdirectly purified by reverse phase HPLC
additiondiluted with ethyl acetate
washwashed with saturated aqueous sodium bicarbonate solution
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ba86b3e25705455f9f134ec8e7aa037e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431569B2

Reaction notes

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