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Acetic Acid → 5-[2-[1-[3-[2-E-(7-Chloroquinolin-2-yl)ethenyl]benzyl]-2,3-dihydroindol-7-yl]ethyl]-1H-tetrazole

HRID 54530
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HRID 54530 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]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 4984872Tributyltin azideHCID 153379297-(2-Cyanoethyl)-1-[3-[2-E-(7-chloroquinolin-2-yl)ethenyl]benzyl]-2,3-dihydroindole

생성물 1

HCID 1784778715-[2-[1-[3-[2-E-(7-Chloroquinolin-2-yl)ethenyl]benzyl]-2,3-dihydroindol-7-yl]ethyl]-1H-tetrazole
수율 36%

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

  1. washwashed with hexane
  2. customThe hexane layer was separated
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. customthe residue chromatographed (silica gel, 2% methanol/98% methylene chloride)
  5. customto provide a solid
  6. customthat was recrystallized (ethyl acetate/ether)

출처 및 근거

ORD 기록
ord-9d50b99de78b49ec8c57758e0904db2b
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05622969

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