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

Participants

Role	Name	HCID	Charge
Reactant	2-(5-Bromofuran-2-yl)-8-methyl-imidazo[1,2-a]pyridine-6-carbonitrile	HCID 69252117	—
Reactant	2-[5-(4-Cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrile	HCID 69253840	—
Reactant	2-[5-(4-Amidinophenyl)-furan-2-yl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-6-carboxamidine acetate salt	HCID 69254384	—
Product	2-[5-(4-Cyanophenyl)-furan-2-yl]-8-methyl-imidazo[1,2-a]pyridine-6-carbonitrile	HCID 69252035	77%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07432278B2
Source dataset	uspto-grants-2008_10
ORD ID	ord-caeefecbf661425e8a219fb6e81f263f
Source note	uspto-grants-2008_10