반응 #60217

반응 방정식

ethyl 6-chloro-4-phenylpyridine-3-carboxylate

(2-aminoethyl)(5-nitro(2-pyridyl))amine

Hünig's base

DMA

→

ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate

수율 70.0%

용매

EtOAc

반응 조건

후처리

1. 1
   세척washed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml)
2. 2
   건조dried with Na2SO4
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The yellow solid was purified by column chromatography
6. 6
   기타The product was dried overnight in vacuo

실험 절차

The crude material above, ethyl 6-chloro-4-phenylpyridine-3-carboxylate (140 mg, 0.56 mmol) was mixed with (2-aminoethyl)(5-nitro(2-pyridyl))amine (408 mg, 2.24 mmol), Hünig's base (390 ul), and DMA (2 ml) for 48 hours at 70-75° C. with stirring under argon. The reaction was followed by TLC and HPLC. When judged complete, the reaction was diluted with EtOAc (100 ml) and washed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The yellow solid was purified by column chromatography using 5% MeOH in CH2Cl2 as the eluent. The product was dried overnight in vacuo giving ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate in 70% yield.

출처