Benzylamine → HCID 178420324, Verbindung

HRID 45923

Reaktionsgleichung

Reaktionsgleichung von HRID 45923
Br[C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:11]([NH:18][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Produkt 1

HCID 178420324HCID 178420324, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), benzylamine (128 mg; 0.127 ml; 1.2 mmol; 1.2 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (9 mg; 0.024 mmol; 0.024 eq.; 2.4 mol %), Pd2 dba3 (9 mg; 0.01 mmol; 0.01 eq.; 1 mol %) and lithiumbis(trimethylsilyl)amide 1 M in THF (2.2 ml; 2.2 mmol; 2.2 eq.) according to method 1; Yield: 0.150 g (67.3%); MS m/z: 224.5 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.33 (s, 2H); 6.64 (d, 1H, 4J=2.1 Hz); 6.98 (dd, 1H; 4J=2.1 Hz, 3J=8.9 Hz); 7.23-7.38 (m, 5H); 7.51 (d, 1H, 3J=8.9 Hz); 8.07 (s, 1H); HPLC (METHOD [A]): rt 22.19 min (80.6%)

Aufarbeitung

  1. customThe compound was synthesized
  2. customrt 22.19 min (80.6%)

Quellen und Nachweise

ORD-Eintrag
ord-ad029776530146eeb0133adb9c59f6c8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541596B2

Verknüpfte Notizen

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