Methanol → HCID 58443263, compound

HRID 1630750Notes

Reaction equation

HRID 1630750 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[C:5]([Cl:15])=[CH:4][N:3]=1.CO.C(N(CC)CC)C.[C]=O.C[CH2:28][O:29][C:30](C)=[O:31]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:15][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:7][C:2]([C:30]([O:29][CH3:28])=[O:31])=[N:3][CH:4]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 58443288HCID 58443288, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 58443263HCID 58443263, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
100 °C

Procedure

To a mixture of 2,5-dichloro-4-(3-fluorophenyl)pyridine (0.604 g, 2.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (dppf) (0.105 g, 0.19 mmol), and Pd(OAc)2 (0.025 g, 0.11 mmol) was added MeOH (3.5 mL) and triethylamine (0.365 mL, 2.6 mmol). The nitrogen atmosphere was replaced with carbon monoxide (3.4 atm) and the reaction mixture was heated to 100° C. in a sealed tube. After 17 h, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave methyl 5-chloro-4-(3-fluorophenyl)picolinate.

Workup

  1. washwashed with saturated NaHCO3 (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-71961a7f472541269a6a64aba88d3ced
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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