tert-Butanol → 1-(6-Morpholino-2',3',5',6'-tetrahydrospiro-[indoline-3,4'-pyran]-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

1-(6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone (2.56 g, 8.25 mmol) was combined with morpholine (1.08 mL, 12.4 mmol), dicyclohexyl-(2′,4′,6′-triisopropylbiphenyl-4-yl)phosphine (0.118 g, 0.248 mmol), Pd2dba3 (0.256 g, 0.248 mmol), and cesium carbonate (4.03 g, 12.4 mmol) in tert-butanol (30.0 mL, 314 mmol). The reaction was purged with N2, and heated at 110° C. for 4 h. After this time the reaction was diluted with EtOAc and filtered through a Celite pad. The filtrate was concentrated in vacuo. The crude material was triturated with EtOAc/hexane to give 1-(6-morpholino-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran]-1-yl)ethanone. Mass Spectrum (ESI) m/e=317 (M+1).

Provenance & Evidence