Dichloromethane → HCID 68323762, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	4-tert-Butylphenylboronic acid	HCID 2734320	—
Reactant	N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide	HCID 68324076	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	HCID 68323762	HCID 68323762	45.3%

Reaction Conditions

Temperature	150 °C

Reaction Steps

Under nitrogen, N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 61) (100 mg, 0.232 mmol) was dissolved in toluene (2 mL) and [4-(1,1-dimethylethyl)phenyl]boronic acid (61.9 mg, 0.347 mmol), PdCl2(dppf).DCM (18.91 mg, 0.023 mmol) and Cs2CO3 (226 mg, 0.695 mmol) were added. The mixture was then heated in a microwave at 150° C. for 30 min. Water (10 mL) was added and the mixture extracted with ethyl acetate (3×10 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, to give the title compound (51 mg). LCMS (A) m/z: 485 [M+1]+, Rt 1.70 min (basic).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029545B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-a06296bc4eb8430489458693afbd7710
Source note	uspto-grants-2015_05