참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | 2-Bromo-5-methoxybenzaldehyde | HCID 344480 | — |
| 반응물 | 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole | HCID 18525700 | — |
| 촉매 | HCID 178418397 | HCID 178418397 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde | HCID 58542002 | 65.2% |
반응 단계
To a solution of 2-bromo-5-methoxybenzaldehyde (200 mg, 0.93 mmol) in DMF (10 mL) and H2O (2 mL) are added 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (333 mg, 1.4 mmol), Pd(PPh3)4 (107 mg, 0.09 mmol) and K2CO3 (257 mg, 1.9 mmol) at room temperature. The solution is heated to 120° C. for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and is filtered. The filtrate is washed with H2O (10 mL) and is extracted with EtOAc (3×10 mL). The combined organic layer is dried, (MgSO4), filtered and is concentrated and the residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde (150 mg, 65%) as a white foam.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08420655B2 |
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| 출처 데이터셋 | uspto-grants-2013_04 |
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| ORD ID | ord-e10d6363990b4126980d57e36b3d770c |
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| 출처 메모 | uspto-grants-2013_04 |
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