2-Bromopyridine → 1-(Pyridin-2-yl)-1H-imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)-furan-2-yl]ethyl}amide

HRID 872456Notes

Reaction equation

HRID 872456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH2:14][CH2:15][NH:16][C:17]([C:19]3[N:20]=[CH:21][NH:22][CH:23]=3)=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH2:14][CH2:15][NH:16][C:17]([C:19]3[N:20]=[CH:21][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH:23]=3)=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 1785231341H-Imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide

Product 1

HCID 706567111-(Pyridin-2-yl)-1H-imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)-furan-2-yl]ethyl}amide

Procedure

The title compound was synthesized from 1H-Imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide of Example 15 and 2-bromopyridine by the method described by A. K. Verma et al. Tetrahedron Lett. 48 (2007) 4207. Purification by flash chromatography using CH2Cl2/MeOH as a gradient eluent (100:0-99.9:0.1) gave a product which was triturated in EtOAc at RT to afford the desired product. 1H NMR (400 MHz, DMSO-d6): 2.96 (2H, t), 3.59 (2H, m), 6.35 (1H, d), 7.03 (1H, d), 7.44 (1H, m), 7.63 (2H, s), 7.84 (1H, s), 7.95 (1H, distorted d), 8.05 (1H, m), 8.33 (1H, t), 8.43 (1H, d), 8.54 (1H, m), 8.64 (1H, d, 4J=1.1 Hz).

Workup

  1. customPurification by flash chromatography
  2. customgave a product which
  3. customwas triturated in EtOAc at RT

Sources & evidence

ORD record
ord-5ae656f128b3403da7218763ff23d666
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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