Dimethylformamide → HCID 58645689, compound

HRID 545077Notes

Reaction equation

HRID 545077 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([O:12][CH3:13])[N:3]=1.[Cl-].[NH4+].[OH-].[NH4+].[CH3:18][N:19](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:13][O:12][C:4]1[N:3]=[C:2]([C:18]#[N:19])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 150913542-Chloro-6-Methoxy-3-(trifluoroMethyl)pyridine

Product 1

HCID 58645689HCID 58645689, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×

Procedure

Heat a solution of 2-chloro-6-methoxy-3-trifluoromethyl-pyridine (211 mg, 1.0 mmol), zinc cyanide (64 mg, 0.55 mmol), pd2(dba)3 (45 mg), DPPF (55 mg) in DMF (3 mL) and water (0.03 mL), under a nitrogen atmosphere, at 120° C. for 1.5 hours. Cool the reaction to 0° C. and add a solution of saturated ammonium chloride solution (2 mL), water (2 mL) and concentrated ammonium hydroxide (0.5 mL) and stir for 1 hour. Extract the mixture with ethyl acetate (3×20 mL) and wash the combined organics with brine (50 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with a 25:1 mixture of hexane:ether to give the title compound.

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. extractionExtract the mixture with ethyl acetate (3×20 mL)
  4. washwash the combined organics with brine (50 mL)
  5. customDry the
  6. extractionorganic extract over MgSO4
  7. customremove the solvent under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with a 25:1 mixture of hexane

Sources & evidence

ORD record
ord-9e42791737324acb81b87468724b19ed
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

Loading…