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Cesium carbonate → Methyl 5-(3-chlorophenyl)nicotinate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Methyl 5-bromopyridine-3-carboxylate | HCID 699336 | — |
| 反応物 | 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 10037225 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | Methyl 5-(3-chlorophenyl)nicotinate | HCID 20099850 | 80.5% |
反応手順
104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of 3-chlorophenylboronic acid pinacol ester 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.14 g (72%) of 5-(3-Chloro-phenyl)-nicotinic acid methyl ester
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07429605B2 |
| 出典データセット | uspto-grants-2008_09 |
| ORD ID | ord-48cf15a1bb314f92a712ee4b2305e794 |
| 出典メモ | uspto-grants-2008_09 |