Indole → HCID 50993869, compound

Participants

Reaction Conditions

Reaction Steps

To a 30 mL vial equipped with stir-bar was added 0.400 g (0.71 mmol) 4-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole followed by 0.096 g (0.78 mmol) 3-pyridinyl boronic acid, 3 mL toluene, 3 mL ethanol, 0.71 mL 2 M aqueous sodium carbonate and 0.011 g (0.035 mmol) tetra n-butylammonium bromide. The starting indole did not dissolve, so 3 mL DME (ethylene glycol dimethyl ether) were added. The reaction mixture was degassed for 30 min by bubbling nitrogen into the mixture. Pd(PPh3)4 (0.018 g, 0.022 mmol) was added and the reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled and filtered through Celite®, washing with ethyl acetate. The solvent was removed and the crude product was purified by preparative TLC (eluent: 30:70 ethyl acetate:hexane) to give 0.184 g of 4-[3-(4-methoxy-benzyloxy)-5-pyridin-3-yl-phenyl]-1-triisopropylsilanyl-1H-indole. This compound was deprotected as described in Example 34. 1H NMR (400 MHz, CDCl3): δ 10.07 (d, J=2.1 Hz, 1H), 9.74 (dd, J=4.9, 1.3 Hz, 1H), 9.30 (dt, J=4.9, 2.6 Hz, 1H), 8.70 (q, J=4.3 Hz, 1H), 8.65-8.61 (m, 2H), 8.53 (d, J=3.3 Hz, 1H), 8.45-8.36 (m, 3H), 8.29 (t, J=1.9 Hz, 1H), 7.89 (d, J=3.1 Hz, 1H).

Provenance & Evidence