関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Pyrazole | HCID 1048 | — |
| 反応物 | Sodium Chloride | HCID 5234 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-Bromo-2-methoxyaniline | HCID 459257 | — |
| 反応物 | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | N-methyl-2-pyrrolidone | HCID 13387 | — |
| 生成物 | 2-Methoxy-4-(1H-pyrazol-1-yl)aniline | HCID 59794359 | 90% |
反応手順
To a solution of 4-bromo-2-(methyloxy)aniline (400 mg, 1.979 mmol) in anh. NMP (4 mL), at r.t., under N2, were added pyrazole (269 mg, 2 eq), K2CO3 (819 mg, 3 eq), CuI (377 mg, 1 eq) and (1R,2R)-diaminomethylcyclohexane (281 mg, 1 eq). The reaction mixture was stirred at 150° C. for 3 hr. It was cooled down to r.t. and poured into EtOAc/sat.aq. NaCl. The phases were separated and the organic layer was washed with sat.aq. NH4Cl (20 mL) and sat.aq. NaCl (20 mL). The combined aqueous layers were extracted back with EtOAc (20 mL) and the combined organic extracts were dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3) to give the title compound as a brown oil (336 mg, 90%)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07427630B2 |
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| 出典データセット | uspto-grants-2008_09 |
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| ORD ID | ord-9dae480e5d5e4f97b07f3895141283dc |
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| 出典メモ | uspto-grants-2008_09 |
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