참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Iodoethane | HCID 6340 | — |
| 반응물 | 4-Benzyloxyaniline | HCID 22860 | — |
| 반응물 | Sodium hydride | HCID 24758 | — |
| 반응물 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 반응물 | Calcium Chloride | HCID 5284359 | — |
| 반응물 | Sodium t-butoxide | HCID 23676156 | — |
| 반응물 | Tert-butyl 2,5-dichloropyridin-3-ylcarbamate | HCID 86660673 | — |
| 촉매 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 용매 | Methanol | HCID 887 | — |
| 용매 | Toluene | HCID 1140 | — |
| 용매 | Isopropanol | HCID 3776 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 58577370 | 247.5% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09226921B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_01 |
|---|
| ORD ID | ord-4fd417b5b42d41e683f9a8691422d1a4 |
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| 출처 메모 | uspto-grants-2016_01 |
|---|
