(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole → (E)-2-[2-(Cyclohexyl)ethenyl]-5-fluoro-1-(2-pyridyl)-1H-benzimidazole

HRID 50942Notes

Reaction equation

HRID 50942 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([NH2:15])[CH:3]=1.[CH:16]1(/[CH:22]=[CH:23]/[C:24](Cl)=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[CH:16]1(/[CH:22]=[CH:23]/[C:24]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:5]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=3[N:15]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 12542153(E)-3-cyclohexylacryloyl chlorideHCID 227367454-fluoro-2-amino-N-(2-pyridyl)aniline

Product 1

HCID 9883594(E)-2-[2-(Cyclohexyl)ethenyl]-5-fluoro-1-(2-pyridyl)-1H-benzimidazole

Procedure

The titled compound was prepared from 4-fluoro-2-amino-N-(2-pyridyl)aniline and (E)-3-Cyclohexylacryloyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 321.40; mp: 109.1-110.1° C.; 1H-NMR (CDCl3) δ: 8.76-8.72 (1H, m), 7.97 (1H, ddd, J=7.7, 7.7, 2.0 Hz), 7.47-7.40 (3H, m), 7.34 (1H, dd, J=9.0, 4.8 Hz), 7.11 (1H, dd, J=15.7, 7.1 Hz), 6.97 (1H, ddd, J=9.0,9.0,2.5 Hz), 6.38 (1H, dd, J=15.7, 1.3 Hz), 2.27-2.10 (1H, m), 1.84-1.57 (5H, m), 1.37-1.09 (5H, m).

Sources & evidence

ORD record
ord-c57c25ab5e8145cbbf49787ab4cbd7ad
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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