Hydrochloric Acid → (E)-1-(6-Fluoropyridin-2-yl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50874

Reaction equation

HRID 50874 reaction equation
[CH:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[ClH:49]>CCOCC>[ClH:49].[F:18][C:19]1[N:20]=[C:21]([N:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=[C:9]2/[CH:1]=[CH:2]/[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 739342,6-DifluoropyridineHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736651(E)-1-(6-Fluoropyridin-2-yl)-2-styryl-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 2,6-difluoropyridine according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method B). The free base was dissolved into diethyl ether and hydrogen chloride gas was passed through the ether solution. Filtration and drying under vacuum yielded the titled compound as pale yellow solids. MW: 351.81; mp: 198.0-205.0° C.; 1H-NMR (DMSO-d6) δ: 8.43 (1H, ddd, J=8.1, 8.1, 8.1 Hz), 8.26 (1H, d, J=16.1 Hz), 7.90-7.80 (2H, m), 7.76-7.69 (2H, m), 7.66-755 (3H, m), 7.54-7.43 (4H, m), 7.28 (1H, d, J=16.1 Hz).

Workup

  1. filtrationFiltration
  2. customdrying under vacuum

Sources & evidence

ORD record
ord-0bc055b36fde4321966e8386c9ed2cc7
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

Loading…