Tetrabutylammonium Fluoride → 3-(5-Hydroxy-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrile

HRID 1777188Notes

Reaction equation

[Si]([O:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[N:14]=[C:13]([CH:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:28]#[N:29])[CH:26]=4)[NH:21][C:20]3=[O:30])[CH:12]=[CH:11][C:10]1=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1.C(OCC)(=O)C>[OH:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[N:14]=[C:13]([CH:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:28]#[N:29])[CH:26]=4)[NH:21][C:20]3=[O:30])[CH:12]=[CH:11][C:10]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3-(5-(tert-butyldimethylsilyloxy)-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrile (26 mg, 0.062 mmol) in tetrahydrofuran (5 mL) was cooled to 0° C. To this mixture was added dropwise a 1.0M solution of TBAF in THF (0.124 ml, 0.124 mmol) resulting in a clear yellow solution. The reaction was stirred for 1 h at 0° C. and then warmed to RT. After 3 h another portion of TBAF (1.0M in THF, 0.124 ml, 0.124 mmol) was added and the reaction was stirred at RT for 16 h. The mixture was diluted with ethyl acetate and the organic layer was washed with water (2×) and brine (1×). The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. The crude was purified by flash chromatography (silica gel, DCM/MeOH) yielding a yellow solid. Amount 11 mg. Yield 59%.

Workup

customresulting in a clear yellow solution
temperaturewarmed to RT
stirringthe reaction was stirred at RT for 16 h
washthe organic layer was washed with water (2×) and brine (1×)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customevaporated to dryness
customThe crude was purified by flash chromatography (silica gel, DCM/MeOH)
customyielding a yellow solid

Sources & evidence

ORD record: ord-953e83ded9e348688cf9a65808ecb4bd
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266855B2

Reaction notes

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