p-Bromophenoxyacetic acid → {4'-[3-(Propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yloxy}-acetic acid

関与物質

役割	名称	HCID	仕込み量
反応物	p-Bromophenoxyacetic acid	HCID 74657	—
反応物	4-Iodophenoxyacetic acid	HCID 74658	—
反応物	Barium hydroxide	HCID 6093286	—
反応物	Propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide	HCID 59747992	—
触媒	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
溶媒	Water	HCID 962	—
溶媒	Dichloromethane	HCID 6344	—
溶媒	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
生成物	{4'-[3-(Propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yloxy}-acetic acid	HCID 69253225	65%

反応手順

Heat a solution of (4-Iodo-phenoxy)-acetic acid or (4-bromo-phenoxy)-acetic acid (0.25 mmol), propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (122 mg, 0.30 mmol), PdCl2(dppf)(41 mg, 0.05 mmol) and barium hydroxide (158 mg, 0.50 mmol) in DMF-H2O (v/v 4:1, 2.5 mL) to 80° C. under nitrogen atmosphere for 20 h. Pour into H2O (50 mL) and dichloromethane (50 mL), then extract with H2O (4×50 mL) and dry the combined organic phases (MgSO4). Concentrate to furnish a crude mixture as a yellowish solid. Purification by flash chromatography (Silica gel-Hexane/EtOAc) affords the title compound as a pale yellow solid (65-80% yield). MS (ES−):430.1 (M−1).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07393868B2
出典データセット	uspto-grants-2008_07
ORD ID	ord-c9bc2a267f5f4f9f8e14a35b2bf89860
出典メモ	uspto-grants-2008_07