Dichloromethane → (2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[5-(4-piperazin-1-ylphenyl)pyridin-2-yl]methoxy}pentanamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	[4-(Piperazin-1-yl)phenyl]boronic acid	HCID 5233013	—
Reactant	(2S)-2-[(5-bromopyridin-2-yl)(phenyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide	HCID 86605403	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[5-(4-piperazin-1-ylphenyl)pyridin-2-yl]methoxy}pentanamide	HCID 86605402	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

(2S)-2-[(5-bromopyridin-2-yl)(phenyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide from example 53 step 3 (156 mg, 0.375 mmol), 4-piperazine-1-ylphenyl boronic acid (100 mg, 0.413 mmol, 1.1 eg), [1,1′-Bis(diphenylphosphino)-ferrocene dichloropalladium II complex with CH2Cl2 (13.7 mg, 0.0187 mmol, 0.05 eg), sodium carbonate (2M soln, 750 uL, 1.5 mmol, 4 eg) were mixed together in DMF (5 mL). The reaction mixture was degased 3× with N2, then heated to 90° C. for 5 hours. After cooling, the mixture was evaporated under high vacuum and residue was chromatographed with a mixture of dichloromethane/methanol/ammonium hydroxide (90:9:1) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07279478B2
Source dataset	uspto-grants-2007_10
ORD ID	ord-30ef33e6592f416d83a33151d253d1ae
Source note	uspto-grants-2007_10