Diisopropylethylamine → Methyl 4-{1-[({1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoate

Beteiligte Stoffe

Reaktionsschritte

Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate (30.8 g, 97 mmol), HATU (38.6 g, 101 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (24.9 g, 130 mmol) were added to DMF (483 ml). The solution was cooled in an ice bath and DIPEA (50.6 ml, 290 mmol) was added. The mixture was aged overnight at RT and 500 ml of EtOAc was added. The mixture was then poured into 2 L of NaHCO3 (½ sat.). The layers were cut and the aqueous layer was washed 2 more times with DCM. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 9.18 (s, 1H), 7.75 (m, 3H), 7.60 (d, 2H), 7.45 (d, 1H), 7.40 (d, 1H), 7.20 (d, 2H), 7.15 (t, 1H), 6.90 (d, 2H), 6.65 (d, 1H), 5.70 (s, 2H), 3.85 (s, 3H), 1.20 (m, 2H), 0.95 (m, 2H).

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