Sodium Carbonate → HCID 44479928, Verbindung

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:15])[C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH:16]1([CH2:19][NH:20][C:21](=[O:37])[C:22]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH:8]1([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH2:19][CH:16]4[CH2:18][CH2:17]4)=[O:37])=[CH:23][CH:24]=3)[C:13]([CH3:14])=[C:12]([F:15])[CH:11]=2)=[O:6])[CH2:10][CH2:9]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

3-Bromo-N-cyclopropyl-5-fluoro-4-methylbenzamide (Intermediate 1, 40 mg, 0.15 mmol), N-cyclopropylmethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (45 mg, 0.15 mmol) and tetrakis(triphenylphosphine)palladium (17 mg, 0.015 mmol) were dissolved in DME (3 ml) and aqueous sodium carbonate (1M, 150 μl) was added. The mixture was refluxed at 80° C. for 16 hours. Solvent was removed in vacuo and the residue was purified by silica biotage chromatography, eluting with ethyl acetate:cyclohexane (2:) then 100% ethyl acetate to give N3-cyclopropyl-N4′-(cyclopropylmethyl)-5-fluoro-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide (34 mg, 62%)

Aufarbeitung

customSolvent was removed in vacuo
customthe residue was purified by silica biotage chromatography
washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-f58b1fbc22574c159912e0e29d9f6b55
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07208629B2

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