Morpholine → 5-Morpholin-4-yl-1-(2-trimethylsilanylethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 51 (1.48 g, 4.52 mmol), morpholine (0.473 mL, 5.43 mmol), Pd2(dba)3 (0.083 g, 0.090 mmol), Xantphos (0.157 g, 0.271 mmol) and t-BuONa (0.652 g, 6.78 mmol) in toluene (15 mL) was heated at 100° C. for 2.5 hours. The mixture was cooled and poured into brine and extracted with AcOEt. The organic layer was washed with brine, dried (MgSO4), and concentrated. The residue was purified by means of SGC with hexane: AcOEt as eluent to afford 52 (0.81 g, 54%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.94-1.00 (m, 2H), 3.18-3.23 (m, 4H), 3.57-3.63 (m, 2H), 3.96-4.02 (m, 4H), 5.70 (s, 2H), 6.50 (d, J=0.35 Hz, 1H), 7.38 (d, J=0.35 Hz, 1H), 7.55 (d, J=0.26 Hz, 1H), 8.24 (d, J=0.26 Hz, 1H).

Provenance & Evidence