Reaktion #74209

Reaktionsgleichung

lithiumbis(trimethylsilyl)amide

5-bromobenzimidazole

4-fluorobenzylamine

THF

2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

→

N-(4-Fluorobenzyl)-3H-benzo[d]imidazol-5-amine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe compound was synthesized
2. 2
   Sonstigert 11.21 min (99.2%)

Vorschrift

The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), 4-fluorobenzylamine (150 mg; 0.137 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: 0.096 mg (39.8%); MS m/z: 242.4 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.25 (s, 2H); 6.04 (br s, 1H); 6.50 (s, 1H); 6.59 (dd, 1H, 4J=1.2 Hz, 3J=8.5 Hz); 7.09-7.13 (m, 2H); 7.26 (d, 1H, 3J=8.5 Hz); 7.38-7.41 (m, 2H); 7.83 (s, 1H); 11.88 (br s, 1H); HPLC (METHOD [A]): rt 11.21 min (99.2%)

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