反応 #61564

反応方程式

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

収率 55.2%

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

収率 55.2%

溶媒

water

DMF

反応条件

後処理

1. 1
   温度was heated at 100° C. for an additional 2 h
2. 2
   温度The reaction mixture was cooled to ambient temperature
3. 3
   抽出extracted with EtOAc (5 mL×3)
4. 4
   洗浄The organic solution was washed with water and brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The crude product was purified by radial chromatography (2 mm SiO2; 3% MeOH in CH2Cl2)

実験手順

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.

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