참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Diisopropylamine | HCID 7912 | — |
| 반응물 | N,N-Dimethylpropargylamine | HCID 81643 | — |
| 반응물 | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| 반응물 | 2-Bromo-5-nitrobenzotrifluoride | HCID 136198 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | Bis(benzonitrile)palladium chloride | HCID 498840 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | Dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine | HCID 67021317 | — |
반응 단계
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).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08030311B2 |
|---|
| 출처 데이터셋 | uspto-grants-2011_10 |
|---|
| ORD ID | ord-48463f684ac441b68d3df8c38e2b99c5 |
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| 출처 메모 | uspto-grants-2011_10 |
|---|
