関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diisopropylamine | HCID 7912 | — |
| 反応物 | Ethyl 5-bromopyridine-3-carboxylate | HCID 140785 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | (2-Fluoro-4-methylphenyl)boronic acid | HCID 2783132 | — |
| 反応物 | Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate) | HCID 6099338 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | Ethyl 5-(2-fluoro-4-methylphenyl)nicotinate | HCID 67338384 | 102.1% |
反応手順
To a solution of ethyl 5-bromonicotinate (0.58 g, 2.53 mmol) in acetonitrile (15 mL) and water (5 mL) were added (2-fluoro-4-methylphenyl)boronic acid (0.47 g, 3.04 mmol), 3,3′,3″-phosphinidynetris(benzenesulfonic acid) trisodium salt (0.22 g, 0.38 mmol), palladium(II)acetate (28.4 mg, 0.13 mmol) and diisopropylamine (0.90 mL, 6.32 mmol). The mixture was heated to 80° C. After 1 h, the mixture was cooled to ambient temperature and saturated aqueous NaHCO3 was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (0.67 g). MS 260.1 (M+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08598209B2 |
|---|
| 出典データセット | uspto-grants-2013_12 |
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| ORD ID | ord-394117abaf164211983341ba147be7a0 |
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| 出典メモ | uspto-grants-2013_12 |
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