Nitrogen → HCID 57987541, compound

HRID 1869735Notes

Reaction equation

HRID 1869735 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[CH:6]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.N#N>C1(C)C=CC=CC=1.CCOC(C)=O.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.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:21][CH:20]=2)[CH:6]=1

Participants

9

Reactant 5

HCID 947NitrogenHCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 24729490Methyl (2-chloropyridin-4-yl)acetate

Product 1

HCID 57987541HCID 57987541, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl(2-chloropyridin-4-yl)acetate (1.0 g, 5.4 mmol), 4-(trifluoromethoxy)phenylboronic acid (1.67 g, 8.0 mmol) and potassium phosphate (1.7 g, 8.0 mmol) in toluene (15 ml) was degassed, evacuated and N2 filled (×3). [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (H), complex with DCM (1:1) (330 mg, 0.4 mmol, 5 mol %) was added and following a further degassing, evacuation and N2 fill (×3), the mixture was heated at reflux for 16 hours. The reaction was cooled to room temperature and diluted with EtOAc (100 ml). The mixture was filtered through a Celite® pad, washing through with EtOAc and the filtrate was evaporated. The residue was purified by chromatography on silica, eluting with 15-20% EtOAc/isohexane to give the ester (1.25 g, 75%) as a pale gum. 1H NMR (400 MHz, CDCl3) δ: 3.70 (2H, s), 3.74 (3H, s), 7.20 (1H, dd, J 1.5, 5.0), 7.31 (2H, d, J 8.8), 7.64 (1H, s), 8.00-8.04 (2H, m), 8.64 (1H, d, J 5.0).

Workup

  1. customwas degassed
  2. customevacuated
  3. additionN2 filled (×3)
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 16 hours
  6. filtrationThe mixture was filtered through a Celite® pad
  7. washwashing through with EtOAc
  8. customthe filtrate was evaporated
  9. customThe residue was purified by chromatography on silica
  10. washeluting with 15-20% EtOAc/isohexane

Sources & evidence

ORD record
ord-133d83c7e39345bc81cdf4fec6fb8f03
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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