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Potassium Fluoride → N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide

HRID 1360872
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1360872
I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].[F-].[K+].CC1(C)C(C)(C)OB([C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)O1>C1(C)C=CC=CC=1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][C:3]1[N:4]=[C:5]([NH:7][C:8](=[O:10])[CH3:9])[S:6][C:2]=1[C:22]1[CH:26]=[CH:25][S:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 522689Potassium FluorideHCID 27605974,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolaneHCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamide

Produkt 1

HCID 11993592N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 887MethanolLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a microwave tube, N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (564.2 mg; 2 mmol; 1 eq) and Pd(dppf)Cl2 (73.2 mg; 0.10 mmol; 0.05 eq) are suspended in Toluene (7 ml). A solution of potassium fluoride (464.8 mg; 8 mmol; 4 eq) in MeOH (7 ml) is added. 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (630.3 mg; 3 mmol; 1.50 eq) is finally added as a solid. The resulting solution is flushed with argon, the tube is closed and heated under microwave action at 120° C. for 15 minutes. The reaction mixture is filtered over Celite and the solvents are evaporated. The resulting crude product is dissolved in EtOAc, washed with water and brine and dried over MgSO4. It is then purified by preparative HPLC, affording the title compound as white-off solid (316.7 mg; 66% yield).

Aufarbeitung

  1. customThe resulting solution is flushed with argon
  2. customthe tube is closed
  3. filtrationThe reaction mixture is filtered over Celite
  4. customthe solvents are evaporated
  5. dissolutionThe resulting crude product is dissolved in EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. customIt is then purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ccf3eacb5e914cfc8305ec894d642762
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07879888B2

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