2-Amino-5-bromopyridine → 4-(6-Bromoimidazo[1,2-a]pyridin-2-yl)benzonitrile

HRID 2113558Notes

Reaction equation

HRID 2113558 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[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][N:32]=1>CCO>[Br:37][C:34]1[CH:35]=[CH:36][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

5

Reactant 3

HCID 706222-Amino-5-bromopyridineHCID 986544-(Bromoacetyl)benzonitrileHCID 692538532-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile

Product 1

HCID 674039434-(6-Bromoimidazo[1,2-a]pyridin-2-yl)benzonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The same procedure described for 3a was used employing 4-Cyanophenacyl bromide and 2-Amino-5-bromopyridine. Yield 62%, mp 218-219° C. (EtOH). 1H NMR (DMSO-d6); δ 7.41 (d, J=8.7 Hz, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.90 (d, J=8.4 Hz, 2H), 8.15 (d, J=8.4 Hz, 2H), 8.53 (s, 1H), 8.92 (s, 1H). 13C NMR; δ 143.5, 143.0, 137.9, 132.7, 128.5, 127.1, 126.1, 118.8, 117.9, 111.3, 110.0, 106.4. MS (m/z, rel.int.); 298 (M+, 100). Anal. (C14H8BrN3) C, H.

Sources & evidence

ORD record
ord-ea1a7d728a604f40b3da0c91ab2e4c7d
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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