반응 #1256873

반응 방정식

lithium bromide

(1-Methyl-1H-1,2,4-triazol-5-yl)methyl methanesulfonate

4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

sodium hydride

→

titled product

4-(3-Fluorophenyl)-6-methoxy-1-[(1-methyl-1H-1,2,4-triazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoline-3-carbonitrile

용매

N,N-dimethylformamide

1,2-dimethoxyethane

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITAfter one hour
2. 2
   기타the reaction was quenched with water
3. 3
   기타partitioned between EtOAc and water
4. 4
   세척the organic layer was washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude product was crystallized from EtOAc/hexane

실험 절차

To a solution of 4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (46.0 mg, 0.156 mmol) in 2 mL of 1,2-dimethoxyethane and 0.5 mL of N,N-dimethylformamide at 0° C. was added sodium hydride (8.0 mg of 60% dispersion in mineral oil, 0.23 mmol). After 10 minutes, lithium bromide was added (27 mg, 0.31 mmol), and the reaction was stirred for one hour. A solution of (1-Methyl-1H-1,2,4-triazol-5-yl)methyl methanesulfonate (33 mg, 0.17 mmol) in 0.5 mL of N,N-dimethylformamide was added, and the reaction was allowed to warm to room temperature. After one hour, the reaction was quenched with water and partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was crystallized from EtOAc/hexane to provide the titled product. 1H NMR, difference nOe, and HMQC NMR spectral data for the product were consistent with the titled compound. HRMS (ES) exact mass calculated for C21H16FN5O2 (M+H+): 390.1361. Found 390.1409.

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