Diisopropylethylamine → 2-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide

Participants

Reaction Conditions

Reaction Steps

(R)-1-(tert-Butyldimethylsilyloxy)-4-(2-iodo-1-triethylsilyloxy-ethyl)benzene (J. Org. Chem., vol. 56, p. 442 (1991)) (65 mg, 0.13 mmol) and (R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxyl]-N,N-diethylacetamide (80 mg, 0.26 mmol) and iPr2NEt (115 μL) are dissolved in tetrahydrofuran (2 mL), and the mixture is stirred at 110° C. for 10 hours. After cooling, the mixture is concentrated and the residue is purified by silica gel column chromatography (chloroform→a saturated ammonia solution in chloroform) to give the desired 2-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (42 mg, yield: 48%).

Provenance & Evidence