참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Nitrogen | HCID 947 | — |
| 반응물 | Dichloromethane | HCID 6344 | — |
| 반응물 | Methanesulfonic Acid | HCID 6395 | — |
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | 2-Bromo-3-methylpyridine | HCID 220832 | — |
| 반응물 | (3-((Tert-butoxy)carbonyl)phenyl)boronic acid | HCID 2773299 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Toluene | HCID 1140 | — |
| 생성물 | tert-Butyl 3-(3-methylpyridin-2-yl)benzoate | HCID 57516851 | 82% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09434717B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_09 |
|---|
| ORD ID | ord-00a65a3ffaa5405e921719537369bf38 |
|---|
| 출처 메모 | uspto-grants-2016_09 |
|---|
