Indole → HCID 59004598, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of compound 1 (195 mg, 1.20 mmol), 5-bromopyridin-2-amine (173 mg, 1.00 mmol), copper iodide (9.5 mg, 0.05 mmol) and K3PO4 (400 mg, 2.10 mmol) in toluene (6 mL) was treated with N,N′-dimethylethylenediamine (21.5 μL, 0.20 mmol) then heated at 110° C. overnight. A TLC analysis indicated mostly starting indole and 3-bromopyridine and a new more polar spot. The reaction mixture was treated with additional copper iodide ((9.5 mg, 0.05 mmol) and N,N′-dimethylethylenediamine (21.5 μL, 0.20 mmol). The mixture was heated at 110° C. for 7 hours. After cooling, the mixture was poured into H2O (20 mL) then extracted with CH2Cl2 (100 mL). The organic layer was separated, washed with brine and concentrated to give a yellow solid which was subjected to flash chromatography on silica gel (CH2Cl2 to MeOH:CH2Cl2, 5:95) to give the desired compound 75 (110 mg, 36.1%). 1H NMR (DMSO-d6) δ 8.65 (d, J=2.2 Hz, 1H), 8.10 (d, J=2.7 Hz, 1H), 8.05 (dd, J=2.7, 6.9 Hz, 1H), 7.76 (d, J=3.2 Hz, 1H), 7.60 (dd, J=2.9, 6.0 Hz, 1H), 7.47 (d, J=9.2 Hz, 1H), 6.94 (d, J=3.2 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H); ESI-MS (m/z, %): 255 (M+1, 100%).

Provenance & Evidence