4-Chloropyridine → HCID 43259379, compound

HRID 2373970Notes

Reaction equation

HRID 2373970 reaction equation
[H-].[K+].Cl[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17]C(=O)CC(NC3C=CC(F)=CC=3)=O)=[CH:13][C:12]=2[F:31])[CH:7]=[CH:6][N:5]=1.ClC1C=CN=CC=1>CN(C=O)C>[F:31][C:12]1[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=1[O:10][C:8]1[CH:9]=[CH:4][N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 122884-ChloropyridineHCID 82127Potassium hydrideHCID 59853048HCID 59853048, compound2×

Product 1

HCID 43259379HCID 43259379, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Potassium hydride (30%, 0.520 g, 3.90 mmol, 3.0 eq) was added to a solution of 2-fluoro-4-aminophenol (Compound A of Example 20, 0.254 g, 2.00 mmol, 1.5 eq) in DMF (5.0 mL) at room temperature and the reaction mixture was stirred for 15 minutes. 4-Chloro-pyridine (Aldrich, 0.200 g, 1.30 mmol, 1.0 eq) was added and the reaction mixture was heated to 150° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with 1N NaOH and the solution extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with 1N aqueous NaOH (2×30 mL) followed by 10% aqueous LiCl (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a solid. 1H NMR (DMSO-d6) δ 8.44-8.46 (m, 2H), 6.89-7.03 (m, 1H), 6.87-6.88 (m, 2H), 6.44-6.56 (m, 2H), 5.51 (s, 2H); MS(ESI+) m/z 205 (M+H)+; HRMS(ESI+) calcd.: 205.0777, found: 205.0775.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with 1N NaOH
  3. extractionthe solution extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with 1N aqueous NaOH (2×30 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05cd4fa296d34d92a88e8ba75d3745ea
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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