참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Acrylonitrile | HCID 7855 | — |
| 반응물 | N-Methyl dicyclohexylamine | HCID 24210 | — |
| 반응물 | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| 반응물 | Methyl 3-bromobenzo[b]thiophene-2-carboxylate | HCID 12238750 | — |
| 촉매 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 용매 | Toluene | HCID 1140 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | (E)-Methyl 3-(2-cyanovinyl)benzo[b]thiophene-2-carboxylate | HCID 86647799 | — |
반응 단계
In a flask under nitrogen was placed tris(dibenzylideneacetone)dipalladium(0) (313 mg, 0.34 mmol) in 25 mL of 1,4-dioxane followed by the product obtained from Example 97A (4.5 g, 16.7 mmol), N-methyldicyclohexylamine (3.91 g, 20.0 mmol), tri-tert-butylphosphine (0.68 mL of a 1.0 M solution in toluene, 0.68 mmol) and acrylonitrile (1.06 g, 20.0 mmol). The mixture was stirred and heated at 50° C. under nitrogen for 90 minutes and then cooled and diluted with 100 mL of ethyl acetate and stirred for 15 minutes. The mixture was filtered and the precipitate washed with 25 mL of ethyl acetate. The filtrate was concentrated and worked up as described in Example 55B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.92 (s, 3H) 6.55 (d, J=17.29 Hz, 1H) 7.54-7.66 (m, 2H) 8.13-8.25 (m, 3H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08846951B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_09 |
|---|
| ORD ID | ord-fad7574bf7b346bd8d9f520537762d70 |
|---|
| 출처 메모 | uspto-grants-2014_09 |
|---|
