4-(Bromoacetyl)benzonitrile → 4-(6-Bromo-8-methyl-imidazo[1,2-a]pyridin-2-yl)-benzonitrile

HRID 2113559Notes

Reaction equation

HRID 2113559 reaction equation
BrC1OC(C2N=C3C=CC(C#N)=CN3C=2)=CC=1.[C:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24](=O)[CH2:25]Br)=[CH:22][CH:21]=1)#[N:19].[NH2:30][C:31]1[C:36]([CH3:37])=[CH:35][C:34]([Br:38])=[CH:33][N:32]=1>>[Br:38][C:34]1[CH:35]=[C:36]([CH3:37])[C:31]2[N:32]([CH:25]=[C:24]([C:23]3[CH:28]=[CH:29][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[N:30]=2)[CH:33]=1

Participants

4

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 1379342-Amino-5-bromo-3-methylpyridineHCID 692538532-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile

Product 1

HCID 692545664-(6-Bromo-8-methyl-imidazo[1,2-a]pyridin-2-yl)-benzonitrileYield 71%

Procedure

The same procedure described for 3a was used employing 4-Cyanophenacyl bromide and 2-Amino-5-bromo-3-methylpyridine. Yield 71%, mp 209-210° C. 1H NMR (DMSO-d6); δ 2.56 (s, 3H), 7.53 (s, 1H), 7.95 (d, J=8.1 Hz, 2H), 8.14 (d, J=8.1 Hz, 2H), 8.60 (s, 1H), 8.88 (s, 1H). 13C NMR; δ 143.3, 140.4, 133.3, 133.0, 128.1, 127.4, 127.0, 125.9, 119.2, 112.8, 111.2, 108.2, 16.7. MS (m/z, rel.int.); 312 (M+, 10), 230 (100), 217 (60), 205 (50).

Sources & evidence

ORD record
ord-97a6a893d2254adaa189e343e17e95a8
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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