Tetrahydrofuran → Methyl 5-fluoro-2-methylisonicotinate

HRID 78773Notes

Reaction equation

HRID 78773 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].O1CCC[CH2:14]1.C[Al](C)C.[Cl-].[NH4+]>CCOC(C)=O.CCOC(C)=O.CCCCCC>[F:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]([CH3:14])=[N:11][CH:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 46311206Methyl 2-bromo-5-fluoropyridine-4-carboxylate

Product 1

HCID 58431567Methyl 5-fluoro-2-methylisonicotinate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of methyl 2-bromo-5-fluoroisonicotinate (1.0 g, 4.27 mmol) in tetrahydrofuran (25 ml) tetrakis(triphenylphosphine)palladium (495.0 mg, 0.43 mmol) was added. The mixture was stirred for 10 min, and then trimethylaluminum (5.13 ml, 1.00 M in heptane, 5.13 mmol) was added. The mixture was refluxed for 4 h, and the reaction was monitored by TLC (10% EtOAc-Hexane). Then, the reaction was diluted with EtOAc (75 ml) and a few drops of saturated. ammonium chloride were added.

Workup

  1. temperatureThe mixture was refluxed for 4 h

Sources & evidence

ORD record
ord-94f93ce50ea64b6184b27f57f55d7b80
Source dataset
uspto-grants-2014_09
Patent number
US08841459B2

Reaction notes

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