Pyridine → HCID 67128641, compound

HRID 449927Notes

Reaction equation

HRID 449927 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([F:14])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([Cl:15])[CH:5]=1)(=O)[NH2:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[Cl:15][C:6]1[CH:5]=[C:4]([C:1]#[N:2])[CH:13]=[C:12]([F:14])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 67128745Methyl 4-carbamoyl-2-chloro-6-fluorobenzoate

Product 1

HCID 67128641HCID 67128641, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of methyl 4-carbamoyl-2-chloro-6-fluorobenzoate (2.527 g, 10.9 mmoles) in 1,4-dioxane (25 mL) at room temperature was added pyridine (38.2 mmoles, 3.02 g), followed by trifluoroacetic anhydride (5.04 g, 24.0 mmoles). The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (100 mL), extracted with EtOAc (3×100 mL). The combined organics were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-15% EtOAc/hexane) to afford methyl 2-chloro-4-cyano-6-fluorobenzoate as a white solid (1.953 g, yield: 84%). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=1.1 Hz 1H), 7.37 (dd, J=8.0, 1.2 Hz, 1H), 4.00 (s, 3H). LCMS (APCI+) 214.0 [M+H]+.

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-8484f91fcc9f48e99e43d4c628f32a7a
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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