Réaction #61564

Équation de réaction

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

Rendement 55.2%

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

Rendement 55.2%

Solvants

water

DMF

Conditions de réaction

Traitement

1. 1
   Températurewas heated at 100° C. for an additional 2 h
2. 2
   TempératureThe reaction mixture was cooled to ambient temperature
3. 3
   Extractionextracted with EtOAc (5 mL×3)
4. 4
   LavageThe organic solution was washed with water and brine
5. 5
   Séchagedried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude product was purified by radial chromatography (2 mm SiO2; 3% MeOH in CH2Cl2)

Mode opératoire

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.

Source