関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diisopropylamine | HCID 7912 | — |
| 反応物 | N,N-Dimethylpropargylamine | HCID 81643 | — |
| 反応物 | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| 反応物 | 2-Bromo-5-nitrobenzotrifluoride | HCID 136198 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Bis(benzonitrile)palladium chloride | HCID 498840 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine | HCID 67021317 | — |
反応手順
t-Bu3P (0.25 M in dioxane, 8.9 mL, 2.2 mmol, 0.2 equiv), 3-dimethylamino-1-propyne (FLUKA) (1.65 mL, 15.6 mmol, 1.4 equiv), and i-Pr2NH (2.0 mL, 14.4 mmol, 1.3 equiv) are added sequentially to a mixture of 5-nitro-2-bromobenzotrifluoride (ALDRICH) (3 g, 11.1 mmol), CuI (0.148 g, 0.78 mmol, 0.07 equiv), and Pd(PhCN)2Cl2 (0.427 g, 1.1 mmol, 0.1 equiv) in dioxane (10 mL). The reaction mixture is stirred for 48 h at rt. Then, Pd(PhCN)2Cl2 (0.100 g) is added. After stirring for additional 24 h, the reaction mixture is diluted with EtOAc and H2O and filtered through a pad of Celite. The filtrate is extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude material by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5) affords the title compound as a brown oil: ES-MS: 273.0 [M+H]+; single peak at tR=3.06 min (System 1); Rf=0.13 (CH2Cl2/NH3 (2 N in MeOH), 95:5).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08030311B2 |
|---|
| 出典データセット | uspto-grants-2011_10 |
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| ORD ID | ord-48463f684ac441b68d3df8c38e2b99c5 |
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| 出典メモ | uspto-grants-2011_10 |
|---|
