Potassium Acetate → 3-Chloro-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one

HRID 335853Notes

Reaction equation

HRID 335853 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=[O:17].[F:18][C:19]1[C:24](B(O)O)=[CH:23][CH:22]=[CH:21][N:20]=1.CC([O-])=O.[K+]>>[Cl:12][C:10]1[N:9]=[CH:8][C:7]2[O:13][C:14]3[C:4]([C:5](=[O:17])[C:6]=2[CH:11]=1)=[CH:3][C:2]([C:24]1[C:19]([F:18])=[N:20][CH:21]=[CH:22][CH:23]=1)=[CH:16][CH:15]=3

Participants

4

Reactant 3

HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one

Product 1

HCID 866584693-Chloro-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one

Conditions

Temperature
120 °C

Procedure

A vial was charged with 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (3 g, 9.66 mmol), 2-fluoropyridin-3-ylboronic acid (1.497 g, 10.63 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(H) (0.684 g, 0.966 mmol), and KOAc (1.510 mL, 24.15 mmol). The vial was evacuated and backfilled with nitrogen (this procedure was repeated twice). ACN (20 mL), dioxane (30 mL) and water (3 mL) were added, and the vial was sealed and the reaction mixture was heated to 120° C. for 4 h. The reaction mixture was cooled to RT. Upon addition of EtOAc, a solid precipitated which was filtered off and dried under vacuum to provide 3-Chloro-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one as a tan solid.

Workup

  1. customThe vial was evacuated
  2. additionACN (20 mL), dioxane (30 mL) and water (3 mL) were added
  3. customthe vial was sealed
  4. temperatureThe reaction mixture was cooled to RT
  5. additionUpon addition of EtOAc
  6. customa solid precipitated which
  7. filtrationwas filtered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3a4342dfbacd4b87a1c8b52b69e05cee
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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