Sodium bis(trimethylsilyl)amide → HCID 68737330, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0M THF solution of NaHMDS (158 mL, 158 mmol) at −78° C. was added dropwise to a stirred solution of 2-oxoindoline-4-carbonitrile (6.0 g, 37.3 mmol) in THF (100 mL) under N2. After stirring at −78° C. for 30 minutes, N-benzylbis(2-chloroethyl)amine hydrochloride (10.9 g, 41.2 mmol) was added as a solid. The reaction mixture was stirred at −78° C. for 30 minutes and then allowed to warm to room temperature. The reaction mixture was then heated to reflux for 12 hours. After cooling to 0° C., the reaction was quenched by the addition of saturated aqueous NH4Cl solution. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×200 mL). The combined organics layers were washed with brine, dried with MgSO4 and concentrated. The residue was purified by column chromatography (1:1 hexanes:EtOAc to EtOAc to give 1′-benzyl-2-oxospiro{indoline-3,4′-piperidine]-4-carbonitrile (4.90 g, 50%) as a solid. LCMS (APCI+) m/z 318 [M+H]+; Rt=2.41 min.

Provenance & Evidence