Dichloromethane → 3-Chloro-N-{6-methyl-3-[3-(methyloxy)phenyl]-2-phenylthieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide	HCID 53250396	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-Chloro-N-{6-methyl-3-[3-(methyloxy)phenyl]-2-phenylthieno[2,3-b]pyridin-4-yl}-benzenesulfonamide	HCID 68324149	56.6%

Reaction Steps

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (50 mg, 0.095 mmol) (Example 33), phenylboronic acid (13.97 mg, 0.115 mmol), sodium carbonate (20.23 mg, 0.191 mmol) and PdCl2(dppf).DCM (3.90 mg, 4.77 μmol) in DMF (1 mL) and water (250 μl) was heated at 90° C. under nitrogen, for 3.5 h. The reaction mixture was then cooled to RT and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in DCM, afforded the title compound (28 mg). LCMS (A) m/z: 521 [M+1]+, Rt 1.57 min (acidic), Rt 0.98 min (basic).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029545B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-48bfe2d2e7374c748054cfe2268fb855
Source note	uspto-grants-2015_05