1-Methylimidazole → 2-(4-chlorophenyl)-3-((1-methyl-1H-imidazol-2-yl)methyl)imidazo[1,2-a]pyridine

HRID 455125Notes

Reaction equation

HRID 455125 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[Cl:25]C1C=CC(C2N=C3C=CC=CN3C=2C=O)=CC=1.CN1C=CN=C1>>[Cl:25][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][N:6]3[C:8]=2[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 27577932-(4-Chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehydeHCID 670290646-fluoro-2-(4-fluorophenyl)-3-((1-methyl-1H-imidazol-2-yl)methyl)imidazo[1,2-a]pyridine

Product 1

HCID 670288112-(4-chlorophenyl)-3-((1-methyl-1H-imidazol-2-yl)methyl)imidazo[1,2-a]pyridineYield 19%

Procedure

The title compound was prepared according to Method C and the experimentals described for compound 199 from 2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde and 1-methyl-1H-imidazole. (21.6 mg, 19% yield). M/e+ 323.1 for C18H15ClN4 (M+H)+; 1H-NMR (300 MHz, DMSO, δ) 8.25 (d, J=6.9 Hz, 1H), 7.75 (dd, J=8.7, 2.1 Hz, 2H), 7.61 (d, J=9.0 Hz, 1H), 7.51 (dd, J=8.4, 1.8 Hz, 2H), 7.28 (t, J=2.1 Hz, 1H), 7.08 (d, J=0.9 Hz, 1H), 6.91 (t, J=6.9 Hz, 1H), 6.68 (d, J=0.9 Hz, 1H), 4.53 (s, 2H), 3.58 (s, 3H).

Sources & evidence

ORD record
ord-6349e7e05f5342808a92c88547ebea00
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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