2-(5-Bromofuran-2-yl)-8-methyl-imidazo[1,2-a]pyridine-6-carbonitrile → 2-[5-(4-Cyanophenyl)-furan-2-yl]-8-methyl-imidazo[1,2-a]pyridine-6-carbonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[N:15]=[C:16]4[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][N:17]4[CH:24]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Br[C:26]1OC(C2N=C3C(C)=CC(C#N)=CN3C=2)=CC=1.C(O)(=O)C.C(C1C=CC(C2OC(C3N=C4CCC(C(N)=N)CN4C=3)=CC=2)=CC=1)(=N)N>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[N:15]=[C:16]4[C:21]([CH3:26])=[CH:20][C:19]([C:22]#[N:23])=[CH:18][N:17]4[CH:24]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]Participants
4
Reactant 3
Product 1
Procedure
The same procedure described for 4a was used starting with 3b. Yield 77%, mp 276-277° C. 1H NMR (DMSO-d6); δ 2.54 (s, 3H), 7.12 (d, J=3.6 Hz, 1H), 7.38 (s, 1H), 7.39 (d, J=3.6 Hz, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.99 (d, J=8.4 Hz, 2H), 8.45 (s, 1H), 9.19 (s, 1H). 13C NMR; δ 151.1, 149.7, 144.9, 137.2, 133.6, 132.8, 132.0, 127.4, 123.8, 123.3, 118.8, 117.0, 111.4, 111.0, 110.3, 109.3, 97.1, 16.3. MS (m/z, rel.int.); 324 (M+, 100), 295 (7), 222 (8), 194 (15), 162 (15). High resolution mass calcd. for C20H12N4O: 324.10111. Observed: 324.10070.
Sources & evidence
- ORD record
- ord-caeefecbf661425e8a219fb6e81f263f
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432278B2
Reaction notes
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