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对溴苯氧乙酸 → {4'-[3-(Propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yloxy}-acetic acid
参与物
| 角色 | 名称 | HCID | 投料 |
|---|---|---|---|
| 反应物 | 对溴苯氧乙酸 | HCID 74657 | — |
| 反应物 | 对碘苯氧乙酸 | HCID 74658 | — |
| 反应物 | 氢氧化钡 | HCID 6093286 | — |
| 反应物 | Propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide | HCID 59747992 | — |
| 催化剂 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶剂 | 聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] | HCID 962 | — |
| 溶剂 | 二氯甲烷 | HCID 6344 | — |
| 溶剂 | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| 产物 | {4'-[3-(Propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yloxy}-acetic acid | HCID 69253225 | 65% |
反应步骤
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).
来源与证据
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 专利号 | US07393868B2 |
| 来源数据集 | uspto-grants-2008_07 |
| ORD ID | ord-c9bc2a267f5f4f9f8e14a35b2bf89860 |
| 来源说明 | uspto-grants-2008_07 |