Sodium Bromide → Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoate

HRID 2177712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177712
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(C)C(C)(C)OB([C:33]2[O:37][CH:36]=[N:35][CH:34]=2)O1.O.[F-].[K+].[Br-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:33]3[O:37][CH:36]=[N:35][CH:34]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 253881Sodium BromideHCID 23675105Potassium fluoride hydrateHCID 534270915-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-oxazoleHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2×

Produkt 1

HCID 67107532Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.1 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxazole (0.071 g), tetrakis-(triphenylphosphine) palladium (0.028 g), potassium fluoride monohydrate (0.102 g) and sodium bromide (0.045 g) in toluene (2 ml) was heated in a sealed tube under nitrogen at 125° C. for 18 hours. The mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoate (0.075 g) as a yellow gum.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Quellen und Nachweise

ORD-Eintrag
ord-025f47b8a83f4e668573a70bd0d335ba
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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