Dichloromethane → N-(2-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)propan-2-yl)ethanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile	HCID 57926113	—
Reactant	N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide	HCID 59578400	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(2-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)propan-2-yl)ethanesulfonamide	HCID 49820278	2.8%

Reaction Steps

A mixture of N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide (30 mg, 0.098 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (27.0 mg, 0.103 mmol), PdCl2(dppf).CH2Cl2 adduct (1.994 mg, 2.441 μmol) and sodium carbonate (98 μl, 0.195 mmol) in DMF (10 mL) was heated to 100° C. overnight. After concentration, the residue was purified by column (MeOH—CH2Cl2, v/v, 10-20%) yielded the title compound as oil (1 mg). ESI-MS m/z: [M+1]+364.0, Retention time=1.40 min. 1H NMR (400 MHz, CDCl3): δ 1.31 (t, J=7.37 Hz, 3H), 1.76 (s, 6H), 2.86-2.91 (m, 21-1), 4.54 (brs, 1H), 7.52 (dd, J=1.7, 8 Hz, 1H), 7.67 (d, J=1.6 Hz, 1H), 7.72 (d, J=8 Hz, 1H), 7.95 (t, J=2.2 Hz, 1H), 8.67 (d, J=2.2 Hz, 1H), 8.76 (d, J=2.2 Hz, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08383827B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-6060b30a7fbe47ec8c959d94aed66043
Source note	uspto-grants-2013_02