Triphenylphosphine → HCID 118497062, compound

HRID 522140Notes

Reaction equation

HRID 522140 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[N:13]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:21]([F:26])([F:25])C([O-])=O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[C:21]([F:26])[F:25])[N:13]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2734985Sodium chlorodifluoroacetateHCID 118497008HCID 118497008, compound

Product 1

HCID 118497062HCID 118497062, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 2-chloro-5-(6-formylpyridin-2-yl)benzoate (Preparation 39, 302 mg, 1.10 mmol) in DMF (5.5 mL) was added sodium chlorodifluoroacetate (250 mg, 1.64 mmol) and triphenylphosphine (435 mg, 1.64 mmol) and heated to 120° C. for 40 minutes followed by cooling to room temperature for 2 hours. The reaction was concentrated in vacuo and partitioned between water and EtOAc. The aqueous layer was washed with EtOAc (2×10 mL) and the organic layers combined, washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-20% EtOAc in heptanes to afford the title compound.

Workup

  1. temperatureby cooling to room temperature for 2 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. custompartitioned between water and EtOAc
  4. washThe aqueous layer was washed with EtOAc (2×10 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified
  9. washeluting with 0-20% EtOAc in heptanes

Sources & evidence

ORD record
ord-70ea05a16ea644e3a9d7973d222915d7
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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