5-(4-[1,3]Dioxolan-2-yl-2-fluorophenoxy)pyridine-2-carboxamide → 5-(2-Fluoro-4-formylphenoxy)pyridine-2-carboxamide

HRID 492443Notes

Reaction equation

HRID 492443 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)=[C:8]([F:22])[CH:7]=1>C(O)=O.O>[F:22][C:8]1[CH:7]=[C:6]([CH:2]=[O:1])[CH:21]=[CH:20][C:9]=1[O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=1

Participants

4

Reactant 1

HCID 597301875-(4-[1,3]Dioxolan-2-yl-2-fluorophenoxy)pyridine-2-carboxamide

Product 1

HCID 597299375-(2-Fluoro-4-formylphenoxy)pyridine-2-carboxamideYield 99.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

Take up 5-(4-[1,3]dioxolan-2-yl-2-fluorophenoxy)pyridine-2-carboxamide (0.316 g, 1.04 mmol) in 88% formic acid (5.2 mL). Stir at room temperature for 1.25 hours before diluting with water. Extract with dichloroethane (2× 50 mL). Wash the organic layer with brine (1× 25 mL), dry over Na2SO4, filter and concentrate to give the title compound (0.269 g, 99.6%): TOF MS ES+ 261.1 (M+H)+, HRMS calcd for C13H10N2O3F 261.0675 (M+H)+, found 261.0682, time 0.37 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR 9.0 min, 100% purity.

Workup

  1. extractionExtract with dichloroethane (2× 50 mL)
  2. washWash the organic layer with brine (1× 25 mL)
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5c8e47c4478e4a58beb2ac136c7d28a6
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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