Reaction equation
[H-].[Na+].[Cl-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10]>CS(C)=O>[CH2:9]([O:11][C:12]([C@@H:13]1[CH2:4][C@H:14]1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)=[O:25])[CH3:10]Participants
Procedure
To a suspension of sodium hydride (71 mg, 1.76 mmol) in DMSO (3 mL) under nitrogen atmosphere was added trimethylsulfoxonium chloride (261 mg, 2.03 mmol). After stirring at room temperature for 30 minutes, a solution of 3-quinolin-6-yl-acrylic acid ethyl ester (200 mg, 0.881 mmol) in DMSO (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 2.5 h and quenched with a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine (3×) and adsorbed on silica gel. Purification on silica gel with 0-80% gradient of ethyl acetate in hexane provided 126 mg of product as a white solid. NMR 500 MHz (DMSO) δ 1.22 (t, 3H), 1.55 (m, 2H), 2.10 (m, 1H), 2.64 (m, 1H), 4.13 (q, 2H), 7.50 (dd, 1H), 7.58 (dd, 1H), 7.80 (d, 1H), 7.93 (d, 1H), 8.26 (dd, 1H), 8.84 (dd, 1H); MS (m/z) 242 [M+H+]+.
Workup
- stirringThe reaction mixture was stirred at room temperature for 2.5 h
- customquenched with a saturated aqueous solution of ammonium chloride
- extractionThe mixture was extracted with ethyl acetate (2×)
- washthe combined organic layers were washed with brine (3×)
- customPurification on silica gel with 0-80% gradient of ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-9dc7e8a11d014e5e835963c5cedf1807
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071581B2
Linked notes
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