Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Benzenesulfinic acid → 5-amino-1-(chloromethyl)-3-((5,6,7-trimethoxyindol-2-yl)carbonyl)-1,2-dihydro-3H-benz(e)indole
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Benzenesulfinic acid | HCID 12057 | — |
| 반응물 | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| 반응물 | Sodium | HCID 5360545 | — |
| 반응물 | N-allyl-1-(chloromethyl)-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2-dihydro-3H-benzo[e]indol-5-amine | HCID 9806196 | — |
| 촉매 | HCID 178418397 | HCID 178418397 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 생성물 | 5-amino-1-(chloromethyl)-3-((5,6,7-trimethoxyindol-2-yl)carbonyl)-1,2-dihydro-3H-benz(e)indole | HCID 391700 | 80% |
반응 단계
Benzenesulfinic acid, sodium salt (25 mg, 0.15 mmol) and camphorsulfonic acid (40 mg, 0.17 mmol) were added to a solution of 10a (30 mg, 0.059 mmol) in dichloromethane (5 mL). Pd(Ph3P)4 (5 mg, 0.004 mmol) was added and the reaction mixture was stirred at an ambient temperature for 30 min. The mixture was purified directly via a silica gel column. Elution with EtOAc/petroleum ether (1:1) gave 1-(chloromethyl)-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2-dihydro-3H-benzo[e]indol-5-amine (11a) (22 mg, 80%), spectroscopically identical to an authentic sample (Atwell et al., J. Org Chem., 1998, 63, 9414).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07235578B2 |
| 출처 데이터셋 | uspto-grants-2007_06 |
| ORD ID | ord-8b7c7778a33449fcb86436e46f8aedca |
| 출처 메모 | uspto-grants-2007_06 |