Morpholine → 3,3,7-Trimethyl-6-morpholinoindolin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-3,3,7-trimethylindolin-2-one (0.63 g, 2.44 mmol), NaOt-Bu (0.33 g, 3.42 mmol), Pd2(dba)3 (0.11 g, 0.12 mmol), morpholine (0.51 mL, 5.86 mmol), and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.11 mL, 0.29 mmol) in Toluene (2.5 mL) was flushed with N2 for 10 minutes and then heated in a microwave at 120° C. for 80 minutes. The mixture was cooled to rt and concentrated. Purification of the residue by flash chromatography over silica gel, using 40% EtOAc in hexane, gave 3,3,7-trimethyl-6-morpholinoindolin-2-one. 1H-NMR (DMSO-d6) δ 10.27 (1H, s), 7.04 (1H, d, J=8.0 Hz), 6.64 (1H, d, J=8.0 Hz), 3.72 (4H, s), 2.78 (4H, s), 2.13 (3H, s), 1.21 (6H, s). Mass Spectrum (ESI) m/e=261.1 (M+1).

Provenance & Evidence