1,2-Dimethoxyethane → HCID 57770606, Verbindung

HRID 2091822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091822
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6](Br)[CH:5]=1.COCCOC.[CH:25]1([CH2:28][N:29]2[C:33](B(O)O)=[CH:32][CH:31]=[N:30]2)[CH2:27][CH2:26]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.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.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([C:33]2[N:29]([CH2:28][CH:25]3[CH2:27][CH2:26]3)[N:30]=[CH:31][CH:32]=2)[CH:5]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 57770642HCID 57770642, VerbindungHCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

Produkt 1

HCID 57770606HCID 57770606, VerbindungAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (1.0 g, 3.27 mmol) and palladium tetrakis(triphenylphosphine) (0.189 g, 0.164 mmol) were added to 25 mL DME, and the mixture was stirred at 60° C. for 10 minutes. 1-Cyclopropylmethyl-1H-pyrazole-5-boronic acid (0.65 g, 3.92 mmol) was added, followed by a solution of K3PO4 (1.39 g, 6.54 mmol) in 5 mL water. The mixture was refluxed for six hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (3:1 EtOAc/hexanes) to give 1.14 g of 3-(2-cyclopropylmethyl-2H-pyrazol-3-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=348.

Aufarbeitung

  1. temperatureThe mixture was refluxed for six hours
  2. temperaturecooled to room temperature
  3. custompartitioned between water and EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via flash chromatography (3:1 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f37d830bb28b473bb88904008b07134d
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440673B2

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