Ammonium formate → Ethyl 6-(3,4-difluoro phenoxy)-5-fluoronicotinate

HRID 920355Notes

Reaction equation

HRID 920355 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[C:14]([F:26])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>CO.[Pd]>[F:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[F:24])[O:17][C:15]1[C:14]([F:26])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:16]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86676389Ethyl 2-chloro-6-(3,4-difluorophenoxy)-5-fluoronicotinate

Product 1

HCID 71236611Ethyl 6-(3,4-difluoro phenoxy)-5-fluoronicotinateYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ammonium formate (28.5 g, 452 mmol) and ethyl 2-chloro-6-(3,4-difluorophenoxy)-5-fluoronicotinate (30 g, 90 mmol) in methanol (300 mL) was added Pd/C (3 g, 2.82 mmol). The reaction mixture was stirred at 65° C. for 10 hr. and then filtered. The filtrate was concentrated under reduced pressure to get ethyl 6-(3,4-difluoro phenoxy)-5-fluoronicotinate (20 g, 48.4%).

Workup

  1. filtrationand then filtered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3feea6b5f36e407f8c5146b2e1f0957c
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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