Potassium Carbonate → 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde

HRID 1966685

Reaktionsgleichung

Reaktionsgleichung von HRID 1966685
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:12][C:13]1[S:14][C:15](B2OC(C)(C)C(C)(C)O2)=[C:16]([CH3:18])[N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:12][C:13]1[S:14][C:15]([C:2]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=2[CH:4]=[O:5])=[C:16]([CH3:18])[N:17]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 3444802-Bromo-5-methoxybenzaldehydeHCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

Produkt 1

HCID 585420022-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehydeAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2-bromo-5-methoxybenzaldehyde (200 mg, 0.93 mmol) in DMF (10 mL) and H2O (2 mL) are added 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (333 mg, 1.4 mmol), Pd(PPh3)4 (107 mg, 0.09 mmol) and K2CO3 (257 mg, 1.9 mmol) at room temperature. The solution is heated to 120° C. for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and is filtered. The filtrate is washed with H2O (10 mL) and is extracted with EtOAc (3×10 mL). The combined organic layer is dried, (MgSO4), filtered and is concentrated and the residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde (150 mg, 65%) as a white foam.

Aufarbeitung

  1. temperatureThe solution is cooled down
  2. addition3-mercaptopropyl-functionalized silica gel (500 mg) is added
  3. filtrationis filtered
  4. washThe filtrate is washed with H2O (10 mL)
  5. extractionis extracted with EtOAc (3×10 mL)
  6. dry with materialThe combined organic layer is dried, (MgSO4),
  7. filtrationfiltered
  8. concentrationis concentrated
  9. customthe residue is purified by silica gel flash chromatography
  10. washeluting with 50% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-e10d6363990b4126980d57e36b3d770c
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

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