반응 #61564

반응 방정식

Tricyclic bromide

2-Bromo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

tributyl(phenylethynyl)tin

2,6-di-t-butyl-4-methyl phenol

→

17

수율 55.2%

(Phenylethynyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

수율 55.2%

용매

water

DMF

반응 조건

후처리

1. 1
   온도was heated at 100° C. for an additional 2 h
2. 2
   온도The reaction mixture was cooled to ambient temperature
3. 3
   추출extracted with EtOAc (5 mL×3)
4. 4
   세척The organic solution was washed with water and brine
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude product was purified by radial chromatography (2 mm SiO2; 3% MeOH in CH2Cl2)

실험 절차

Tricyclic bromide 11 (58.6 mg, 0.22 mmol) in DMF (1 mL) was degassed and treated with tributyl(phenylethynyl)tin (95.2 mg, 0.24 mmol) and tetrakis(triphenylphosphine) palladium(0) (13 mg, 2 mol %). One crystal of 2,6-di-t-butyl-4-methyl phenol was added, and the solution was heated at 60° C. for 10 h. Starting material was still present, so the solution was heated at 100° C. for an additional 2 h. The reaction mixture was cooled to ambient temperature and diluted with water (2 mL) and extracted with EtOAc (5 mL×3). The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by radial chromatography (2 mm SiO2; 3% MeOH in CH2Cl2) to yield 17 as a white solid (34.8 mg, 55%). mp 255-256° C. (dec); 1H NMR (DMSO-d6) δ 11.86 (s, 1H), 8.17 (m, 1H), 7.75 (d, 1H, J=7.6 Hz), 7.63 (m, 3H), 7.51 (m, 3H), 7.33 (t, 1H, J=7.6 Hz), 3.50 (m, 2H), 3.09 (m, 2H); HRMS (FAB, M+H) Calcd for C19H14N2O+H: 287.1184, Found: 287.1192; Anal. (C19H14N2O.0.6 H2O) C, H, N.

출처