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Biphenyl → 5-Thiazol-2-yl-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Biphenyl | HCID 7095 | — |
| 反応物 | 2-Bromothiazole | HCID 76430 | — |
| 反応物 | (1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane | HCID 11521263 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 5-Thiazol-2-yl-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester | HCID 66939620 | 52% |
反応手順
A mixture of 2-bromothiazole (200 mg, 1.22 mmol), palladium acetate (15 mg, 0.06 mmol), sodium tert-butoxide (217 mg, 2.26 mmol), (S,S) 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (280 mg, 1.4 mmol) and 2-Di-t-butylphosphino)-biphenyl (37 mg, 0.118 mmol) was stirred in dioxane (10 ml) at 80° C. for overnight. The reaction was cooled, diluted with ethyl acetate (40 ml) and H2O (50 ml). The organic layer was separated, dried (Na2SO4), filtered and solvent evaporated. The residue was purified by chromatography eluting with 5% MeOH/DCM yielding product as a white solid. (180 mg, 52% yield)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08546404B2 |
| 出典データセット | uspto-grants-2013_10 |
| ORD ID | ord-5f0d31b3dc66434a9d00699ec56389b2 |
| 出典メモ | uspto-grants-2013_10 |