1,2-Dichloroethane → HCID 90408338, Verbindung

HRID 594025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594025
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([B:8]([OH:10])[OH:9])[CH:7]=1.[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([OH:21])=O)([CH3:15])([CH3:14])[CH3:13].[CH2:25](Cl)[CH2:26]Cl.ON1[C:34]2N=CC=[CH:38][C:33]=2N=N1.[CH3:39]N(C=O)C>CCOC(C)=O.O>[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([B:8]2[O:10][C:33]([CH3:38])([CH3:34])[C:25]([CH3:26])([CH3:39])[O:9]2)[CH:7]=1)=[O:21])([CH3:13])([CH3:14])[CH3:15]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 181649HOAtHCID 6932922-Tert-butylpyridine-4-carboxylic acidHCID 57497242HCID 57497242, Verbindung

Produkt 1

HCID 90408338HCID 90408338, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-amino-2-methylphenylboronic acid, pinacol ester (1.0 equiv.), 2-(tert-butyl)isonicotinic acid (1.0 equiv.), EDC (1.0 equiv.) and 1-hydroxy-7-azabenzotriazole (0.380 g, 1.0 equiv.) in DMF (0.3 M) was stirred at RT for 68 hr. The reaction mixture was then diluted with EtOAc and water, the organic layer was isolated and the aqueous layer was extracted twice with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated in vaccuo to yield 2-(tert-butyl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isonicotinamide as a white solid in 91%. LCMS (m/z) (M+H)=395.1, Rt=0.71 min.

Aufarbeitung

  1. customthe organic layer was isolated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vaccuo

Quellen und Nachweise

ORD-Eintrag
ord-99309c1b4ff347b181218128b771f694
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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