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

HRID 54530

Reaktionsgleichung

Reaktionsgleichung von HRID 54530
[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

Komponenten

6

Edukt 5

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9d50b99de78b49ec8c57758e0904db2b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622969

Verknüpfte Notizen

Wird geladen…