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5-Aminobenzene-1,3-dicarbonitrile → 3,5-Dicyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 5-Aminobenzene-1,3-dicarbonitrile | HCID 19777619 | — |
| 反応物 | 9-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole | HCID 58142231 | — |
| 反応物 | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 3,5-Dicyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline | HCID 86696081 | 50% |
反応手順
9.0 g of carbazole from step (2b) from Example 2 above and 2.7 g 5-aminoisophthalonitrile were mixed in 50 mL toluene in nitrogen filled glove box. 0.2 g Pd2DBA3 and 0.09 g tri-t-butylphosphinewere added followed quickly by 1.81 g t-BuONa. The mixture was heated briefly to reflux then held at 80° C. overnight in the glove box with vigorous stirring. After cooling the reaction was chromatographed on silica using a gradient of DCM:hexanes (1:4 to 4:1) to elute the product which upon concentration and addition of hexanes precipitated the desired product in 50% yield (˜4 g) with structure confirmed by 1-H nmr spectroscopy.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09276217B2 |
| 出典データセット | uspto-grants-2016_03 |
| ORD ID | ord-86c3656c5d0c45cf98468ef00c29196c |
| 出典メモ | uspto-grants-2016_03 |