반응식
[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](/[CH:21]=[CH:22]/[C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][C:27]([Cl:33])=[CH:28][CH:29]=4)[N:24]=3)[CH:16]=1)[CH2:11][CH2:10]2)#[N:2].C(#N)C.C(O)(=O)C.C1COCC1.C([Sn]([N:59]=[N+:60]=[N-:61])(CCCC)CCCC)CCC>>[Cl:33][C:27]1[CH:26]=[C:25]2[C:30]([CH:31]=[CH:32][C:23](/[CH:22]=[CH:21]/[C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[CH2:14][N:12]3[C:13]4[C:9](=[CH:8][CH:7]=[CH:6][C:5]=4[CH2:4][CH2:3][C:1]4[NH:61][N:60]=[N:59][N:2]=4)[CH2:10][CH2:11]3)=[N:24]2)=[CH:29][CH:28]=1참가 물질
반응물 5
생성물 1
실험 절차
A solution of 7-(2-cyanoethyl)-1-[3-[2-E-(7-chloroquinolin-2-yl)ethenyl]benzyl]-2,3-dihydroindole (600 mg) in tri-n-butyltin azide (2.0 mL) was heated in an oil bath at 95° C. for 23 hours. To the cooled solution was added acetonitrile (50 mL), acetic acid (20 mL), and THF (10 mL). The resulting solution was stirred for 3.5 hours and washed with hexane. The hexane layer was separated and discarded. The resulting mixture was concentrated in vacuo and the residue chromatographed (silica gel, 2% methanol/98% methylene chloride) to provide a solid that was recrystallized (ethyl acetate/ether) to provide 235 mg (36%) of the desired product: mp 141°-144° C. 1H-NMR (DMSO-d6) 8.48 (d, J=9 Hz, 1H), 8.08 (m, 2H), 7.85 (d, J=8 Hz, 1H), 7.75 (d, J=17 Hz, 1H), 7.59 (s, 1H), 7.54 (m, 2H), 7.33 (m, 3H), 7.07 (d, J=8 Hz, 1H), 6.95 (d, J=8 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 4.49 (s, 2H), 3.28 (t, 2H, J=7 Hz), 3.17 (m, 2H), 3.08 (m, 2H), 2.83 (t, J=7 Hz, 2H); MS-FD m/e (493, p).
후처리
- washwashed with hexane
- customThe hexane layer was separated
- concentrationThe resulting mixture was concentrated in vacuo
- customthe residue chromatographed (silica gel, 2% methanol/98% methylene chloride)
- customto provide a solid
- customthat was recrystallized (ethyl acetate/ether)
출처 및 근거
- ORD 기록
- ord-9d50b99de78b49ec8c57758e0904db2b
- 출처 데이터셋
- uspto-grants-1997_04
- 특허 번호
- US05622969
연결된 노트
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