2-[5-(4-Cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrile → 2,6-Bis(4-cyanophenyl)-8-methyl-imidazo[1,2-a]pyridine

HRID 2113560Notes

Reaction equation

HRID 2113560 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](C2OC(C3N=C4C=CC(C#N)=CN4C=3)=CC=2)=[CH:5][CH:4]=1)#[N:2].Br[C:26]1[CH:27]=[C:28]([CH3:43])[C:29]2[N:30]([CH:32]=[C:33]([C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=3)[N:34]=2)[CH:31]=1>>[C:39]([C:38]1[CH:41]=[CH:42][C:35]([C:33]2[N:34]=[C:29]3[C:28]([CH3:43])=[CH:27][C:26]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)=[CH:31][N:30]3[CH:32]=2)=[CH:36][CH:37]=1)#[N:40]

Participants

3

Reactant 2

HCID 692538402-[5-(4-Cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrileHCID 692545664-(6-Bromo-8-methyl-imidazo[1,2-a]pyridin-2-yl)-benzonitrile

Product 1

HCID 692538552,6-Bis(4-cyanophenyl)-8-methyl-imidazo[1,2-a]pyridineYield 73%

Procedure

The same procedure described for 4a was used starting with 20. Yield 73%, mp 283-285° C. 1H NMR (DMSO-d6); δ 2.60 (s, 3H), 7.53 (s, 1H), 7.85-7.93 (m, 6H), 8.17 (d, J=8.4 Hz, 2H), 8.53 (s, 1H), 8.87 (s, 1H). 13C NMR; δ 144.9, 142.5, 141.1, 138.1, 132.6, 132.4, 127.0, 126.6, 126.0, 123.6, 123.3, 122.9, 118.6, 118.4, 111.9, 110.0, 109.7, 16.3. MS (m/z, rel.int.); 335 (M++1, 100), 310 (30), 279 (20), 234 (40).

Sources & evidence

ORD record
ord-6a0c8eae5f9b4246b53d05b7f928ecea
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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