Sodium Carbonate → HCID 90414470, Verbindung

HRID 869020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869020
Br[C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].CC1(C)C(C)(C)OB([C:23]2[NH:27][N:26]=[CH:25][CH:24]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:14][O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([C:23]2[NH:27][N:26]=[CH:25][CH:24]=2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 46311273Ethyl 2-bromo-6-methoxybenzoate

Produkt 1

HCID 90414470HCID 90414470, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a microwave vial was dissolved ethyl 2-bromo-6-methoxybenzoate (500 mg, 1.54 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (330 mg, 1.70 mmol) in DME (10 mL) and water (2 mL). Na2CO3 (259 mg, 3.09 mmol) was then added followed by Pd(PPh3)4 (89 mg, 0.077 mmol) and the reaction mixture was degassed with N2 for 10 minutes. The reaction mixture was then heated at 100° C. for 1 h in the microwave. The mixture was cooled to room temperature, filtered through Celite and washed with EtOAc and DCM. The crude solution was concentrated in vacuo and directly purified via silica gel chromatography (10-80% EtOAc in hexanes) to afford the title compound (125 mg, 33%). MS (ESI) mass calcd. for C13H14N2O3, 246.3. m/z found 247.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) δ 7.63 (d, J=2.2 Hz, 1H), 7.44-7.37 (m, 1H), 7.24 (d, J=8.1 Hz, 1H), 6.94 (dd, J=8.3, 0.9 Hz, 1H), 6.53 (d, J=2.3 Hz, 1H), 4.29 (q, J=7.2 Hz, 2H), 3.88 (s, 3H), 1.25-1.16 (m, 3H).

Aufarbeitung

  1. customthe reaction mixture was degassed with N2 for 10 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. washwashed with EtOAc and DCM
  5. concentrationThe crude solution was concentrated in vacuo
  6. customdirectly purified via silica gel chromatography (10-80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-18568fb50e0a4594b68d9f0d7fddf865
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969352B2

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