Sodium Carbonate → Tert-butyl 4-[3'-(2-{[(cyanomethyl)amino]carbonyl}-1-piperidinyl)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-(4-BOC-Piperazino)phenylboronic acid	HCID 5233014	—
Reactant	1-(3-bromophenyl)-N-(cyanomethyl)-2-piperidinecarboxamide	HCID 22235922	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Tert-butyl 4-[3'-(2-{[(cyanomethyl)amino]carbonyl}-1-piperidinyl)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate	HCID 22236171	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 1-(3-bromophenyl)-N-(cyanomethyl)-2-piperidinecarboxamide (209 mg, 0.65 mmol), 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (219 mg, 0.71 mmol), and PdCl2(dppf) (41 mg, 0.05 mmol) in DMF (4 mL) was heated to 60° C. 2N Na2CO3 (0.65 mL, 1.3 mmol) was added dropwise, and the mixture was heated to 85° C. overnight. The mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with 1 M NaOH and brine, then dried over MgSO4 and concentrated. Purification by flash chromatography (50% EtOAc/hexanes) gave tert-butyl 4-[3′-(2-{[(cyanomethyl)amino]carbonyl}-1-piperidinyl)[1,1′-biphenyl]-4-yl]-1-piperazinecarboxylate.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07012075B2
Source dataset	uspto-grants-2006_03
ORD ID	ord-14a6df670b554437957f0fe0afc01c60
Source note	uspto-grants-2006_03