Binap, (A+-)- → 8-Fluoro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A flask containing 1-chloro-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile (1.50 g, 6.11 mmol), BINAP (570 mg, 0.916 mmol), Pd2(dba)3 (280 mg, 0.305 mmol), and NaOtBu (1.88 g, 19.5 mmol) was evacuated and refilled with nitrogen (×3). Degassed DME (50 mL) and (7R,8R)-7-methyl-1,4-dioxaspiro[4.5]decan-8-amine (1.26 g, 7.33 mmol) were added to the mixture. The reaction mixture was heated to 85° C. overnight, cooled to room temperature, diluted with EtOAc, and washed with water and brine. The organic layer was dried (sodium sulfate), concentrated, and purified by flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C21H21FN4O2) [M+H]+, 381.2. found 381.1.

Provenance & Evidence