Stannane, tributyl-1-cyclohexen-1-yl- → 5-(cyclohex-1-en-1-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

HRID 609731

반응식

HRID 609731 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[C:5]2[CH2:19][CH2:20][N:21]([CH3:23])[CH3:22].C([Sn](CCCC)(CCCC)[C:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=1)CCC>C1(C)C=CC=CC=1>[C:29]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[C:5]3[CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=1

참가 물질

4

반응물 2

HCID 11783615Stannane, tributyl-1-cyclohexen-1-yl-HCID 196004435-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

생성물 1

HCID 196004575-(cyclohex-1-en-1-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole수율 28%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (Example 5a, 109.8 mg 0.30 mmol), 1-tributylstannylcyclohex-1-ene (111 mg, 0.30 mmol) and tetrakistriphenyphosphine palladium (80 mg, 0.07 mmol) in toluene (2 mL) was stirred at 100-110° C. overnight. After removal of the solvent in vacuo, flash chromatography on silica gel (2-10% 2M methanolic ammonia in dichloromethane) yielded 5-(cyclohex-1-en-1-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (31 mg, 28%).

후처리

  1. customAfter removal of the solvent in vacuo, flash chromatography on silica gel (2-10% 2M methanolic ammonia in dichloromethane)

출처 및 근거

ORD 기록
ord-a44e558b88754715ac12449588523e9c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998438

연결된 노트

불러오는 중…