N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide → US10023592, Example 122

Participants

Role	Name	HCID	Charge
Reactant	N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide	HCID 117770988	—
Reactant	3-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one	HCID 123823790	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Bicarbonate Ion	HCID 769	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	US10023592, Example 122	HCID 90019338	35.4%

Reaction Steps

N-[3-Bromo-4-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide (77 mg, 0.2 mmol), the title compound of Example 119, step 2 (50 mg, 0.2 mmol), and Pd(dppf)Cl2 (14 mg, 10%) in 1,4-dioxane (1 mL) and saturated bicarbonate solution (aq) (333 μL) were reacted, worked up and purified in a manner similar to Example 117. The title compound (31 mg, 27%) was obtained as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 1.22 (t, J=7.3, 3 H) 3.11 (q, J=7.3 Hz, 2H) 3.55 (s, 3H) 6.86 (d, J=8.6 Hz, 1H) 7.02-7.12 (m, 1H) 7.13-7.23 (m, 2H) 7.26 (d, J=2.8 Hz, 1H) 7.35-7.52 (m, 1H) 7.60 (m, 1H) 7.79 (s, 1H) 9.48-9.96 (m, 1H). LCMS (M+H)+=439.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-f56c9f245d744610a0be1041e1c2833c
Source note	uspto-grants-2015_08