반응 #479345

반응 방정식

(2R)-4-bromobenzenesulfonic acid-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester

3-(5-cyano-1-methyl-indol-3-yl)propylamine

triethylamine

→

title compound

1-Methyl-3-{3-[(8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)-amino]-proyl}-1H-indole-5-carbonitrile

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with 1N sodium hydroxide
2. 2
   추출extracted with methylene chloride (3×100 mL)
3. 3
   세척The organic layer was washed with water (3×150 mL)
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   기타the solvent was removed under vacuum
7. 7
   기타chromatographed on silica gel (10% methanol-ethyl acetate)
8. 8
   농축The product-containing fractions were concentrated in vacuum

실험 절차

A solution of (2R)-4-bromobenzenesulfonic acid-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (0.5 g, 1.1 mmol), 3-(5-cyano-1-methyl-indol-3-yl)propylamine (0.33 g, 1,4 mmol) and triethylamine (0.23 mL, 2.2 mmol) in dimethylsulfoxide (20 mL) was heated at 90° C. under nitrogen for 16 hours. The reaction mixture was quenched with 1N sodium hydroxide and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. The crude oil was column chromatographed on silica gel (10% methanol-ethyl acetate). The product-containing fractions were concentrated in vacuum to give 0.2 g of the (S)-enantiomer of the title compound as a brown oil. The dihydrochloride salt was prepared in ethyl acetate as a yellow solid (decomposed at 148° C.).

출처