参与物
| 角色 | 名称 | HCID | 投料 |
|---|
| 反应物 | 氨基甲酸叔丁酯 | HCID 77922 | — |
| 反应物 | 2-氯-4-氟吡啶 | HCID 2782792 | — |
| 试剂 | 碳酸氢铯 | HCID 10796 | — |
| 催化剂 | 4,5-双二苯基膦-9,9-二甲基氧杂蒽 | HCID 636044 | — |
| 催化剂 | 三(二亚苄基丙酮)二钯 | HCID 9811564 | — |
| 溶剂 | 1,4-二氧六环 | HCID 31275 | — |
| 产物 | TERT-BUTYL (4-FLUOROPYRIDIN-2-YL)CARBAMATE | HCID 51354888 | 19.46% |
反应步骤
2-chloro-4-fluoropyridine (132 mg, 1 mmol), tert-butyl carbamate (123 mg, 1.05 mmol), CESIUM CARBONATE (652 mg, 2.00 mmol) ,TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (36.6 mg, 0.04 mmol) and 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (46.3 mg, 0.08 mmol) were suspended in 1,4-dioxane (2.5 ml) ,degased with argon and heated to 90 °C for 4 hours. After cooling the reaction was quenched with water and extracted with ethyl acetate ( x 2 ). The combined organic phases were washed with water , a saturated aqueous solution of brine , dried over magnesium sulfate , concentrated then purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford tert-butyl 4-fluoropyridin-2-ylcarbamate (41.3 mg, 19.46 %).
来源与证据
| 来源数据集 | 750 AstraZeneca ELN dataset |
|---|
| ORD ID | ord-79caf81165b848e5b1765189056bb075 |
|---|
| 来源说明 | 750 AstraZeneca ELN dataset |
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