HCID 46311473, compound → HCID 118598708, compound

HRID 1050346Notes

Reaction equation

HRID 1050346 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](NC2N=CN=C(NC(C3CC3)=O)C=2)[C:5](=[O:21])[N:4]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)(C)[NH:23][C:24](=[O:25])[C:3]=12.[Br:34]C1C=C(F)C(C(OCC)=O)=NC=1>[Fe](Cl)(Cl)Cl.C(#N)C>[Br:34][C:6]1[C:5](=[O:21])[N:4]2[CH:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[NH:23][C:24](=[O:25])[C:3]2=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 46311473HCID 46311473, compoundHCID 118598561HCID 118598561, compound

Product 1

HCID 118598708HCID 118598708, compound

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-3-chloro-6-oxo-1H-pyridine-2-carboxamide (1, 0.4 g, 1.59 mmol), 3-fluorobenzaldehyde (2, 0.69 g, 5.57 mmol), acetonitrile (15 mL) and iron(III) chloride (1.81 g, 11.13 mmol) in a sealed tube was heated at 90° C. for 16 h. Once TLC showed consumption of the starting material, the mixture was cooled and filtered through a celite bed. The celite was washed with acetonitrile and the filtrate was concentrated under vacuum. The crude residue was subjected to flash column chromatography eluting with 35% ethyl acetate in hexane. The desired fractions were collected, concentrated and dried under high vacuum to afford 6-bromo-8-chloro-3-(3-fluorophenyl)-2,3-dihydroimidazo[1,5-c]pyridine-1,5-dione (3) as a yellow solid. Yield: 0.35 g, 61%; MS (ESI) m/z 357.20 [M+1]+.

Workup

  1. customconsumption of the starting material
  2. temperaturethe mixture was cooled
  3. filtrationfiltered through a celite bed
  4. washThe celite was washed with acetonitrile
  5. concentrationthe filtrate was concentrated under vacuum
  6. washeluting with 35% ethyl acetate in hexane
  7. customThe desired fractions were collected
  8. concentrationconcentrated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-e0ad80878eeb4b5a9c40c6909b65d55f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…