반응 #720168

반응 방정식

6-(trifluoromethyl)-2-methylpyridine-3-carbonyl chloride

4-chloro-3-(pyridine-2-yl)aniline

EtOAc

→

N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide

수율 88.0%

용매

THF

THF

반응 조건

후처리

1. 1
   세척washed with saturated aq. NaHCO3 (2×), and brine
2. 2
   건조The organics were dried (Na2SO4)
3. 3
   농축concentrated
4. 4
   workup.STIRRINGstirred at 0° C. for ½ hr
5. 5
   여과collected by suction filtration

실험 절차

6-(trifluoromethyl)-2-methylpyridine-3-carbonyl chloride (1.68 g, 7.51 mmol) in 3 mL THF was added dropwise to a solution of 4-chloro-3-(pyridine-2-yl)aniline (1.21 g, 5.93 mmol) in THF (15 mL) at 0° C. The solution was stirred for 10 min., poured into EtOAc and washed with saturated aq. NaHCO3 (2×), and brine. The organics were dried (Na2SO4) and concentrated. The crude product was suspended in iPrOAc/Et2O (10 mL, 1:1), stirred at 0° C. for ½ hr, and collected by suction filtration to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(trifluoromethyl)-2-methylpyridine-3-carboxamide (2.04 g, 5.21 mmol, 88% yield) as a white solid: TLC Rf=0.28 (35% EtOAc/Hex); 1H NMR (CDCl3, 400 MHz) δ 8.88 (bs, 1H), 8.41 (d, 1H), 7.96 (dd, 1H), 7.74 (m, 4H), 7.52 (d, 1H), 7.22 (m, 1H), 2.75 (s, 3H); MS (Q1) 392 (M)+.

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