Water → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine

HRID 911949Notes

Reaction equation

HRID 911949 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12]S(C)(=O)=O)[CH3:11].[N+:17]([C:20]1[N:25]=[CH:24][C:23]2[CH:26]=[CH:27][O:28][C:22]=2[C:21]=1O)([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:21]1[C:22]2[O:28][CH:27]=[CH:26][C:23]=2[CH:24]=[N:25][C:20]=1[N+:17]([O-:19])=[O:18])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 578124576-Nitrofuro[3,2-c]pyridin-7-olHCID 57812619(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonate2×

Product 1

HCID 578124747-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Alternate synthesis: To a solution of Methanesulfonic acid (S)-1-(2,6-dichloro-3-fluorophenyl)-ethyl ester (109 mg, 0.380 mmol) and 6-nitrofuro[3,2-c]pyridin-7-ol (68.4 mg, 0.380 mmol) in DMF (1.0 mL) was added potassium carbonate (57.2 mg, 0.414 mmol), and the resulting suspension was stirred at ambient temperature for 1 h and at 60° C. overnight. Methanesulfonic acid (S)-1-(2,6-dichloro-3-fluorophenyl)ethyl ester (32.7 mg, 0.114 mmol) and potassium carbonate (16 mg, 0.12 mmol) were added to the reaction mixture, and the mixture was heated at 70° C. for 3 days. Water and EtOAc were added to the reaction mixture, the layers were separated, and the aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc extracts were washed with 1N NaOH (2×), water (2×), and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound.

Workup

  1. customAlternate synthesis
  2. temperaturethe mixture was heated at 70° C. for 3 days
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  5. washThe combined EtOAc extracts were washed with 1N NaOH (2×), water (2×), and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6bb30f3a8165421ea1602a8df08f0562
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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