Morpholine → 3,3-Dimethyl-6-morpholinoindoline

Participants

Reaction Conditions

Reaction Steps

The 6-iodo-3,3-dimethylindoline (250 mg, 0.915 mmol), morpholine (0.399 mL, 4.58 mmol), Pd2(dba)3 (33.5 mg, 0.037 mmol), and 2-(dicyclohexylphosphino)-2,4,6-tri-i-propyl-1,1-biphenyl (34.9 mg, 0.073 mmol) were dissolved in THF (2.0 mL) and 1M lithium bis(trimethylsilyl)amide (5.03 mL, 5.03 mmol) solution in THF was added to a sealed tube and heated to 65° C. for 1 h. The reaction was cooled to rt and then poured into water (30 mL) and extracted with EtOAc (1×150 mL) and DCM (1×150 mL). The combined organic layers were dried over magnesium sulfate and the crude product was purified by medium pressure chromatography (silica, 50 to 100% EtOAc:DCM) to give 4-(3,3-dimethylindolin-6-yl)morpholine. Mass Spectrum (ESI) m/e=233.2 (M+1).

Provenance & Evidence