1-(2-Bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzene → US10023592, Example 121

Participants

Role	Name	HCID	Charge
Reactant	1-(2-Bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzene	HCID 118021787	—
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 121	HCID 118021893	27%

Reaction Steps

The title compound of Example 119, step 2 (40 mg, 0.16 mmol), 1-(2-bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzene (60 mg, 0.16 mmol), and Pd(dppf)Cl2 (12 mg, 10%) in 1,4-dioxane (880 μL) and saturated bicarbonate solution (aq) (220 μL) were reacted, worked up and purified in a manner similar to Example 117. The title compound (18 mg, 27%) was obtained as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 1.13 (t, J=7.33 Hz, 3H) 3.34 (q, J=7.33 Hz, 2H) 3.59 (s, 3H) 6.92-6.98 (m, 1H) 7.19-7.27 (m, 1H) 7.50-7.61 (m, 2H) 7.76-7.84 (m, 2H) 7.92-7.96 (m, 1H) 7.97-8.01 (m, 1H) LCMS (M+H)+=424.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-04aa3d8e096d4f76a7e4ee56093e8a67
Source note	uspto-grants-2015_05