Trifluoroacetic acid → HCID 50915293, compound

HRID 1191321Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](CC1C=CC(OC)=CC=1)[C:7](=[O:21])[C:6]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[C:5]2[O:27][CH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.FC(F)(F)C(O)=O>C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:21])[C:6]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[C:5]2[O:27][CH2:28][CH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

Conditions

Temperature: 100 °C

Procedure

6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one (160 mg, 0.30 mmol) was taken into neat trifluoroacetic acid (500 μL, 6.5 mmol). The reaction mixture was heated overnight at 100° C. The crude reaction mixture was poured into saturated sodium bicarbonate (50 mL). The product was extracted with dichloromethane (3×50 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 4:1 dichlormethane/ethyl acetate) to yield 6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-3-(thiophen-2-yl)quinolin-2(1H)-one as an off white solid. LCMS (M+H)=419.8. 1H NMR (400 MHz, CDCl3) 12.0 (s, 1H), 8.00 (s, 1H), 7.88 (d, 1H), 7.62 (d, 1H), 7.54 (d, 1H) 7.30 (d, 1H), 7.18 (t, 1H), 4M (dd, 2H) 3.65 (d, 2H), 3.45 (t, 2H), 2.15 (m, 1H), 1.75 (d, 2H), 1.4 (m, 2H).

Workup

customThe crude reaction mixture
extractionThe product was extracted with dichloromethane (3×50 mL)
extractionThe combined organic extractions
dry with materialwere dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified via flash chromatography (silica, 4:1 dichlormethane/ethyl acetate)

Sources & evidence

ORD record: ord-ba6c747366114807b639fd8bea655016
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680116B2

Reaction notes

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