(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole → (E)-5-Fluoro-2-[2-(3-furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

HRID 50943Notes

Reaction equation

HRID 50943 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:25])[CH2:21][CH2:20]CCC1.N1C=CC=C[C:28]=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[F:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:20](/[CH:21]=[CH:16]/[C:22]3[CH:23]=[CH:24][O:25][CH:28]=3)=[N:15][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 227367454-fluoro-2-amino-N-(2-pyridyl)anilineHCID 566232073-Cyclohexylprop-2-enoyl chloride

Product 1

HCID 22736678(E)-5-Fluoro-2-[2-(3-furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

Procedure

The titled compound was prepared from 4-fluoro-2-amino-N-(2-pyridyl)aniline and (E)-3-(3-Cyclohexylacryloyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 305.31; mp: 168.0-170.0° C.; 1H-NMR (CDCl3) δ: 8.82-8.76 (1H, m), 8.15 (1H, d, J=16.0 Hz), 8.04 (1H, ddd, J=7.7, 7.7, 1.8 Hz), 7.71 (1H, s), 7.60-7.50 (3H, m), 7.43-7.33 (2H, m), 7.05 (1H, ddd, J=9.1, 9.1, 2.5 Hz), 6.74 (1H, d, J=16.0 Hz), 6.53 (1H, s).

Sources & evidence

ORD record
ord-74bf31554aca427f83f8aeec0e68dc79
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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