Potassium Carbonate → N-Boc 4-(6-Cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine

https://huagongshe.com/reaction/1969002

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine	HCID 59444100	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	tert-Butanol	HCID 6386	—
Product	N-Boc 4-(6-Cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine	HCID 59444141	61.9%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A solution of N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine (D135, 100 mg, 0.189 mmol) in anhydrous degassed tert-butanol (2 mL) was treated with X-PHOS (10 mg, 0.021 mmol), potassium carbonate (70 mg, 0.506 mmol), palladium (II) acetate (2 mg, 8.91 μmol), and phenylboronic acid (2 mg, 0.016 mmol), then heated at 85° C. for 1 h then cooled and evaporated. Chromatography on silica (20 g), eluting with 10-50% ethyl acetate—isohexane, gave N-Boc-4-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine (40 mg, 0.117 mmol, 61.8% yield) as a colourless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08426443B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-bca4d0ae9022424d96fcc5280f625300
Source note	uspto-grants-2013_04