Tetrahydrofuran → 4-tert-butyl 1-methyl 2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)succinate

HRID 1427285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427285
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=N[N:13]2[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[H-].[Na+].[CH2:41]1COCC1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:41][N:13]2[C:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:19]([O:21][CH3:22])=[O:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 70563540methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)acetate

Produkt 1

HCID 705860914-tert-butyl 1-methyl 2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)succinate

Versuchsvorschrift

A solution of methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)acetate (2 g, 4.83 mmol), as described in Example 2 Step B, and tert-butyl 2-bromoacetate (1.4 g, 7.25 mmol) in THF (10 mL) was added to NaH (290 mg, 7.25 mmol, 60% in oil) dropwise at 0° C. and stirred for 30 min. The mixture was quenched with saturated NH4Cl solution, and extracted with ethyl acetate. The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE:EA=3:1) to afford the title compound. LC/MS m/z=529.2[M+H]+.

Aufarbeitung

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE:EA=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-66a7c1461b494a43a5b54fa976059d00
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933113B2

Notizen zur Reaktion

Wird geladen…