HCID 87426400, compound → HCID 67510190, compound

HRID 623469Notes

Reaction equation

HRID 623469 reaction equation
C[Zn]C.Cl[C:5]1[N:14]=[C:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].Cl[C:22]1C=CC(C(OC)=O)=C(OCC(F)(F)F)N=1>>[CH3:22][C:5]1[N:14]=[C:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 3

HCID 87426400HCID 87426400, compoundHCID 87427267HCID 87427267, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 67510190HCID 67510190, compoundYield 36%

Conditions

Temperature
75 °C

Procedure

Dimethylzinc (40.0 mL, 40.0 mmol) is added dropwise a solution of methyl 2-chloro-6-(2,2,2-trifluoroethoxy)nicotinate (2.70 g, 10.0 mmol, Step-2) including methyl 6-chloro-2-(2,2,2-trifluoroethoxy)nicotinate and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.816 g, 1.00 mmol) and stirred at 75° C. for 1 hour. After cooling room temperature, the resulting mixture is quenched by carefully added water. The reaction mixture is extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (20:1) to give 0.89 g (36% yield) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling room temperature
  2. customthe resulting mixture is quenched by carefully added water
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-29db273490af4dbebaf5da24d044da38
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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