関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Nitrogen | HCID 947 | — |
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | Methanesulfonic Acid | HCID 6395 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 2-Bromo-3-methylpyridine | HCID 220832 | — |
| 反応物 | (3-((Tert-butoxy)carbonyl)phenyl)boronic acid | HCID 2773299 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | tert-Butyl 3-(3-methylpyridin-2-yl)benzoate | HCID 57516851 | 82% |
反応手順
2-Bromo-3-methylpyridine (1.0 eq) is dissolved in toluene (12 vol). K2CO3 (4.8 eq) is added followed by water (3.5 vol) and the mixture heated to 65° C. under a stream of N2 for 1 hour. 3-(t-Butoxycarbonyl)phenylboronic acid (1.05 eq) and Pd(dppf)Cl2.CH2Cl2 (0.015 eq) are then added and the mixture is heated to 80° C. After 2 hours, the heat is turned off, water is added (3.5 vol) and the layers are allowed to separate. The organic phase is then washed with water (3.5 vol) and extracted with 10% aqueous methanesulfonic acid (2 eq MsOH, 7.7 vol). The aqueous phase is made basic with 50% aqueous NaOH (2 eq) and extracted with EtOAc (8 vol). The organic layer is concentrated to afford crude tert-butyl-3-(3-methylpyridin-2-yl)benzoate (82%) that is used directly in the next step.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08846718B2 |
|---|
| 出典データセット | uspto-grants-2014_09 |
|---|
| ORD ID | ord-84731088f4f743a9ac8c2caf4f96cd92 |
|---|
| 出典メモ | uspto-grants-2014_09 |
|---|
