Oxazole → HCID 57378193, Verbindung

HRID 76018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76018
[Li]CCCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[N:32]2[C:36]([CH3:37])=[C:35](I)[N:34]=[N:33]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>C1COCC1.CCOC(C)=O.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[N:32]2[C:36]([CH3:37])=[C:35]([C:7]3[O:6][CH:10]=[CH:9][N:8]=3)[N:34]=[N:33]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

Komponenten

8

Edukt 3

HCID 9255OxazoleHCID 59428119HCID 59428119, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 57378193HCID 57378193, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cooled (−78° C.) solution of n-BuLi (0.5 mL, 2.5 M solution in hexanes) in THF (3 mL) was added oxazole (0.1 mL, 1.5 mmol) via dropwise addition and the solution was stirred for 30 minutes. ZnCl2 solution (3.9 mL, 0.5 M in THF) was then added and the reaction mixture was warmed to room temperature and stirred an additional 2 hours. Pd(PPh3)4 (20 mg, 0.015 mmol) and 4-tert-butyl-N-[4-chloro-2-(4-iodo-5-methyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide (synthesized according to general procedure P, 77 mg, 0.15 mmol) were then added and the reaction mixture was heated at 80° C. overnight. The reaction mixture was subsequently diluted with EtOAc (25 mL) and the combined organics were washed with water (20 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by preparative TLC to afford the title compound: MS (ES) M+H expected 472.1, found 472.0.

Aufarbeitung

  1. additionvia dropwise addition
  2. stirringstirred an additional 2 hours
  3. temperaturethe reaction mixture was heated at 80° C. overnight
  4. washthe combined organics were washed with water (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-80cc816cf713424db11d18fd5437cf86
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835468B2

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