Réaction #69859

Équation de réaction

2-((1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

2-bromobenzo[d]thiazole

DIPEA

→

title compound

Rendement 59.2%

2-((1H-indol-3-yl)methyl)-9-(benzo[d]thiazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

Rendement 59.2%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   Autrethe residue was purified by flash chromatography (EtOAc/hexane 2:3)

Mode opératoire

To the solution of 2-((1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (60 mg, 0.20 mmol) and 2-bromobenzo[d]thiazole [2516-40-7] (56 mg, 0.26 mmol) in ethanol (0.7 ml) was added DIPEA (176 μl, 1.0 mmol) and DMAP (1.2 mg, 0.01 mmol). The mixture was heated at 160° C. for 1.25 h under microwave conditions. The solvent was evaporated and the residue was purified by flash chromatography (EtOAc/hexane 2:3) to yield 51 mg (56%) of the title compound as a pale yellow solid. [1H NMR (600 MHz, DMSO-d6) ♀ ppm 10.96 (br. s., 1H), 7.76 (d, J=7.9 Hz, 1H), 7.54 (d, J=8.1 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 7.22-7.32 (m, 2H), 7.01-7.11 (m, 2H), 6.96 (t, J=7.3 Hz, 1H), 4.63 (s, 2H), 3.82-3.96 (m, 2H), 3.38-3.49 (m, 2H), 3.17 (t, J=5.9 Hz, 2H), 2.06-2.18 (m, 2H), 1.74-1.84 (m, 2H), 1.61-1.74 (m, 2H), 1.53 (d, J=13.7 Hz, 2H); LCMS RtC=2.37 min, [M+H]+=431.2].

Source