Ethanol → Ethyl 6-[ethoxy(imino)methyl]imidazo[1,2-a]pyridine-2-carboxylate

HRID 2363748Notes

Reaction equation

C([S-])C.[Na+].[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)[CH:12]=1)#[N:6].[CH2:21]([OH:23])[CH3:22]>ClCCl>[CH2:21]([O:23][C:5](=[NH:6])[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)[CH:12]=1)[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

470 mg of sodium ethanethiolate are added to a solution of 1 g of ethyl 6-cyanoimidazo[1,2-a]pyridine-2-carboxylate (J. Med. Chem. (1998), 41(22), 4317) in a mixture of 15 mL of ethanol and 10 mL of dichloromethane cooled to 0° C. The reaction mixture is stirred for 5 hours at 25° C. and filtered, and the filtrate is evaporated to dryness. The residue is chromatographed on silica, eluting with a mixture of dichloromethane and methanol (98/2) to give 625 mg of ethyl 6-[ethoxy(imino)methyl]imidazo[1,2-a]pyridine-2-carboxylate in the form of a pale yellow solid.

Workup

filtrationfiltered
customthe filtrate is evaporated to dryness
customThe residue is chromatographed on silica
washeluting with a mixture of dichloromethane and methanol (98/2)

Sources & evidence

ORD record: ord-51f69c071a124e999f9b43a265fc3a11
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691990B2

Reaction notes

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