P-Anisidine → HCID 67304571, compound

HRID 876179Notes

Reaction equation

HRID 876179 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 67304571HCID 67304571, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

50 mg of 2-fluoro-4-iodopyridine, 33 mg of p-anisidine, 108 mg of K2CO3, 1 mg of Pd(OAc)2 and 6 mg of BINAP were charged into a microwave vial and 2 mL of dry toluene were added and the vial was sealed, evacuated and flushed with Argon. The mixture in the vial was irradiated at 180° C. in a CEM Explorer™ microwave unit for 30 minutes with stirring and the mixture obtained was cooled to r.t. From the mixture obtained solid material was filtered off and washed with 10 mL of CH2Cl2 and solvent from the combined filtrate and washing solvent was evaporated off. The evaporation residue obtained was subjected to flash column chromatography. (2-Fluoro-N-(4-methoxyphenyl)pyridin-4-amine in the form of yellow crystals was obtained.

Workup

  1. additionwere added
  2. customthe vial was sealed
  3. customevacuated
  4. customflushed with Argon
  5. customThe mixture in the vial was irradiated at 180° C. in a CEM Explorer™ microwave unit for 30 minutes
  6. customthe mixture obtained
  7. customFrom the mixture obtained solid material
  8. filtrationwas filtered off
  9. washwashed with 10 mL of CH2Cl2 and solvent from the combined filtrate
  10. washwashing solvent
  11. customwas evaporated off
  12. customThe evaporation residue obtained

Sources & evidence

ORD record
ord-ad2a511f84da4a6b90c52a7f23f33998
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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