Lithium Chloride → 5-(3-(quinolin-3-yl)-1H-indol-5-yl)thiazol-2-amine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of tert-butyl 5-bromo-3-(quinolin-3-yl)-1H-indole-1-carboxylate (104 mg, 0.246 mmol), Pd(PPh3)4 (14 mg, 0.012 mmol), Lithium chloride (83 mg, 1.965 mmol) and DMF (2.0 ml, 0.246 mmol) in a microwave reaction vessel was sealed and heated at 100° C. for 5 min. A solution of tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (240 mg, 0.491 mmol) in DMF (1.0 mL) was then added and the reaction was heated at 100° C. for additional 17 h. The mixture was filtered through a pad of Celite and the filtrate was evaporated to dryness. The above crude product was dissolved in DCM (0.5 mL) followed by the addition of TFA (0.5 mL). The reaction was stirred at RT for 1 h then evaporated in vacuo to dryness. The residue was purified by silica gel chromatography to 5-(3-(quinolin-3-yl)-1H-indol-5-yl)thiazol-2-amine (6.7 mg, 8.0%) as a yellow solid. MS (ESI, pos. ion) m/z: 343 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 6.98 (s, 2H), 7.32 (d, J=9.0 Hz, 1H), 7.38 (s, 1H), 7.48 (d, J=8.5 Hz, 1H), 7.62 (t, J=7.5 Hz, 1H), 7.70 (t, J=7.3 Hz, 1H), 7.98 (s, 1H), 8.00-8.05 (m, 2H), 8.10 (d, J=8.0 Hz, 1H), 8.62 (s, 1H), 9.29 (d, J=2.0 Hz, 1H), 11.65 (s, 1H).

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