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Ethanol → 3-(5-(Tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 4-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid | HCID 16086086 | — |
| 反応物 | N-tert-butyl-5-chloro-3-formylthiophene-2-carboxamide | HCID 86618194 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 溶媒 | Ammonium Chloride | HCID 25517 | — |
| 生成物 | 3-(5-(Tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid | HCID 86618195 | — |
反応手順
A mixture of N-tert-butyl-5-chloro-3-formylthiophene-2-carboxamide (2.40 g, 9.77 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (3.07 g, 11.7 mmol), Pd(PPh3)2Cl2 (0.343 g, 0.488 mmol, Strem), and sodium carbonate (3.11 g, 29.3 mmol) in DME:EtOH:H2O=7:2:3 (36 ml) was heated to 80° C. for 8 hrs. After cooling to RT, the mixture was diluted with sat. aq. NH4Cl and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated over SiO2. Column chromatography (MeOH/CH2Cl2=0→2%) gave the desired product. Yield: 2.31 g.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745449B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-b133b37652714a72aab5df9f27049a73 |
| 出典メモ | uspto-grants-2010_06 |