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3-(Bromomethyl)-1H-indazole, N1-BOC protected → tert-butyl 3-({1-[2-(benzyloxy)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}methyl)-1H-indazole-1-carboxylate

HRID 1375357
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Reaktionsgleichung

Reaktionsgleichung von HRID 1375357
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=2[N:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:4](=[O:30])[CH2:3]1.Br[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[N:34]=1>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N:8]1[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=2[N:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:4](=[O:30])[CH:3]([CH2:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:35]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[N:34]=2)[C:2]1=[O:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
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Komponenten

5

Edukt 2

HCID 108049513-(Bromomethyl)-1H-indazole, N1-BOC protectedHCID 86602390benzyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

Produkt 1

HCID 69426247tert-butyl 3-({1-[2-(benzyloxy)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}methyl)-1H-indazole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a stirring solution of benzyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate (3.45 g, 8.62 mM) in 25 mL DMF at 0° C. was added 1.1 equiv. of 0.5 M solution of KN(TMS)2 in toluene. The resulting solution was stirred 10–30 min, then a solution of tert-butyl 3-(bromomethyl)-1H-indazole-1-carboxylate (2.95 g, 9.48 mM) in 15 mL DMF was added. The resulting solution was stirred 2 h at RT and then quenched with 5 mL of H2O. The reaction mixture was then poured into 50 mL of EtOAc and extracted with H2O (2×50 mL). The organic layer was separated, dried (MgSO4), and the solvents removed in vacuo. The resultant material was purified by silica gel flash column chromatography using methylene chloride/EtOAc 9/1 providing 4.4 g of white solid.

Aufarbeitung

  1. stirringThe resulting solution was stirred 2 h at RT
  2. customquenched with 5 mL of H2O
  3. additionThe reaction mixture was then poured into 50 mL of EtOAc
  4. extractionextracted with H2O (2×50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvents removed in vacuo
  8. customThe resultant material was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b26e42d70eea42e5865160cccb26cdde
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07169773B2

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