3-Bromopyridine → HCID 20346357, compound

HRID 1701708Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[H-].[Na+].Br[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>CN(C)C=O.CC(C)=O>[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:3]1=[O:12]

Participants

Conditions

Temperature: 30 °C

Procedure

7.36 g of 1-methyl-5-chloro-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one were dissolved in 160 ml of hot dimethylformamide and after cooling the solution to 30° C., 4.64 g of a 50% sodium hydride-oil suspension were slowly added thereto. The mixture was stirred at 40°-50° C. for 2 hours and then 80 ml or 128.8 g of 3-bromo-pyridine and 1.5 g of cuprous chloride were added thereto. The mixture was refluxed for 9 hours and was then cooled and evaporated to dryness. The residue was taken up in ammonium hydroxide solution and was filtered. The product was washed with water to obtain 8 g of raw product which was dissolved in acetone. The solution was chromatographed over silica gel and was eluted with acetone. The product was crystallized from 95% ethanol to obtain 5 g of 1-methyl-3-(3-pyridyl)-5-chloro-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one in the form of white needles melting at 206°-208° C.

Workup

temperatureThe mixture was refluxed for 9 hours
temperaturewas then cooled
customevaporated to dryness
filtrationwas filtered
washThe product was washed with water
customto obtain 8 g of raw product which
customThe solution was chromatographed over silica gel
washwas eluted with acetone
customThe product was crystallized from 95% ethanol

Sources & evidence

ORD record: ord-44d60186a0084ce383d5825c8986e043
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04195088

Reaction notes

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