関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Iodoethane | HCID 6340 | — |
| 反応物 | 4-Benzyloxyaniline | HCID 22860 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | Calcium Chloride | HCID 5284359 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | Tert-butyl 2,5-dichloropyridin-3-ylcarbamate | HCID 86660673 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 58577370 | 247.5% |
反応手順
The mixture of tert-butyl (2,5-dichloropyridin-3-yl)carbamate (7.0 g), 4-(benzyloxy)aniline (7.95 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.231 g), Pd2(dba)3 (0.974 g) and sodium tert-butoxide (3.58 g) in toluene (160 mL)-2-propanol (40.0 mL) was stirred at 100° C. under Ar overnight. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give intermediate. To the intermediate in DMF (100 mL) were added NaH (3.19 g) and ethyl iodide (20.75 g). The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2 g) as a colorless solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09226921B2 |
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| 出典データセット | uspto-grants-2016_01 |
|---|
| ORD ID | ord-4fd417b5b42d41e683f9a8691422d1a4 |
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| 出典メモ | uspto-grants-2016_01 |
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