5-Amino-2-chloro-4-fluorophenol → 5-(5-Amino-2-chloro-4-fluorophenoxy)picolinonitrile

HRID 2042043Notes

Reaction equation

HRID 2042043 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.CC(C)([O-])C.[K+].Cl[C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1>CC(N(C)C)=O.O>[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 38339425-Chloro-2-cyanopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 672540795-(5-Amino-2-chloro-4-fluorophenoxy)picolinonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 5-amino-2-chloro-4-fluorophenol (100 mg, 0.619 mmol) in degassed dimethylacetamide (2 mL) was treated with potassium t-butoxide (83 mg, 0.743 mmol) and 5-chloro-2-cyanopyridine (86 mg, 0.619 mmol). The resultant mixture was heated to 80° C. overnight, then cooled to RT and diluted with water (10 mL). The mixture was extracted with EtOAc (30 mL). The organic phase was washed with water (3×30 mL) and brine (30 mL) dried (Na2SO4) and concentrated in vacuo to provide 5-(5-amino-2-chloro-4-fluorophenoxy)picolinonitrile as a dark oil which was used without further purification. MS (ESI) m/z: 264.0 (M+H+).

Workup

  1. extractionThe mixture was extracted with EtOAc (30 mL)
  2. washThe organic phase was washed with water (3×30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc20acba90dd4f6ab8e5be468a08a14e
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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