참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | (2-BOC-aminophenyl)boronic acid | HCID 2773226 | — |
| 반응물 | 3-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyridinecarbonitrile | HCID 66875754 | — |
| 용매 | Methanol | HCID 887 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 용매 | Toluene ethanol | HCID 21863594 | — |
| 생성물 | 3-(Tert-butyldimethylsilyloxy)benzo[f][1,7]naphthyridin-5-amine | HCID 67117688 | — |
반응 단계
A solution of 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-(tert-butyldimethylsilyloxy)picolinonitrile (from step 3) (1.0 eq.) in toluene/ethanol (10:1, 0.2 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100° C. and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexane to give a solid.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08895577B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_11 |
|---|
| ORD ID | ord-e4be732c7b724c7c8ccb2b3d6e61d82a |
|---|
| 출처 메모 | uspto-grants-2014_11 |
|---|
