Sodium Carbonate → HCID 178453037, Verbindung

HRID 1795278Notizen

Reaktionsgleichung

[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.C(=O)([O-])[O-].[Na+].[Na+].[C:15]([O:19][C:20](=[O:30])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1Br)([CH3:18])([CH3:17])[CH3:16].C(=O)(O)[O-].[Na+]>CN(C)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>[NH:1]1[CH:5]=[CH:4][C:3]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][NH:21][C:20](=[O:30])[O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 1H-pyrazol-3-ylboronic acid (156 mg, 1.4 mmol), tetrakis(triphenylphosphine)palladium(0) (242 mg, 0.21 mmol), and sodium carbonate (222 mg, 2.1 mmol) in dimethylformamide (2 ml), was added tert-butyl-2-bromobenzylcarbamate (200 mg, 0.699 mmol). The suspension was stirred at 100° C. for 2 h, cooled to room temperature, poured onto saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate and concentrated in vacuo. The crude material was passed through silica (ISCO, 0–30% ethyl acetate/hexane) to give tert-butyl 2-(1H-pyrazol-3-yl)benzylcarbamate; MS (ES+) M+1 274.1 for C15H19N3O2.

Aufarbeitung

temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe combined organic layers were washed with saturated sodium chloride
dry with materialdried with magnesium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-4c82832018bd4fcbb20988a2d17ff909
Quelldatensatz: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07026324B2

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