3-Fluorobenzaldehyde → HCID 118598772, compound

HRID 1050355Notes

Reaction equation

HRID 1050355 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.FC1C=C(C=CC=1)C=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][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]=12

Participants

4

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 118598561HCID 118598561, compound

Product 1

HCID 118598772HCID 118598772, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 5-bromo-3-chloro-6-oxo-1H-pyridine-2-carboxamide (1, 0.5 g, 1.99 mmol) in acetonitrile (15 mL), 3-fluorobenzaldehyde (0.86 g, 6.96 mmol) and ferric chloride (2.25 g, 13.92 mmol) were added in a vial. The vial was sealed and heated the reaction mass to 85° C. for 16 h. After completion, the reaction mass was cooled to room temperature, filtered through celite bed, washed with 5% methanol in dichloromethane followed by concentration to get crude. The crude was then purified by column chromatography eluting with 5% methanol in dichloromethane to afford 8-chloro-3-(3-fluorophenyl)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione as white solid. Yield: 0.45 g, 63%; MS (ESI) m/z 256.17 [M+1]+.

Workup

  1. additionwere added in a vial
  2. customThe vial was sealed
  3. temperatureAfter completion, the reaction mass was cooled to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with 5% methanol in dichloromethane
  6. concentrationfollowed by concentration
  7. customto get crude
  8. customThe crude was then purified by column chromatography
  9. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7a07ed4d22ad4bf78e766217416cbb16
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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