反応 #603195

反応方程式

NaHCO3

methyl 2,6-dichloro-4-cyanonicotinate

DIPEA

3-(methylthio)aniline

→

title compound

収率 32.1%

Methyl 6-chloro-4-cyano-2-(3-(methylthio)phenylamino)nicotinate

収率 32.1%

溶媒

CH3CN

反応条件

後処理

1. 1
   温度After the mixture was cooled
2. 2
   抽出the mixture was extracted with EtOAc (2×30 mL)
3. 3
   洗浄The organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL)
4. 4
   乾燥were dried over anhydrous Na2SO4
5. 5
   ろ過filtered through SiO2
6. 6
   濃縮The filtrate was concentrated under reduced pressure
7. 7
   洗浄the residue was washed with IPE
8. 8
   ろ過filtered

実験手順

A mixture of methyl 2,6-dichloro-4-cyanonicotinate (340.8 mg, 1.475 mmol), DIPEA (0.3 mL, 1.718 mmol) and 3-(methylthio)aniline (234.8 mg, 1.687 mmol) in CH3CN (5 mL) was stirred at 60° C. for 2 days. After the mixture was cooled, saturated aq NaHCO3 (30 mL) was added and the mixture was extracted with EtOAc (2×30 mL). The organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL), were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure and the residue was washed with IPE and filtered to give the title compound as a yellow solid (157.8 mg). The filtrate was purified by column chromatography (SiO2, hexanes/EtOAc=8/1) to give another crop (135.5 mg) of the title compound as a yellow oil of (total 293 mg, 60%). 1H-NMR (CDCl3) δ ppm 2.52 (s, 3H), 4.05 (s, 3H), 7.00 (s, 1H), 7.03-7.05 (m, 1H), 7.25-7.32 (m, 2H), 7.66-7.67 (m, 1H), 10.51 (br s, 1H). [M+H] calc'd for C15H13ClN3O2S, 334; found, 334.

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