Potassium Carbonate → (S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acid methyl ester

HRID 732438Notes

Reaction equation

HRID 732438 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>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].O1CCOCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 86614996HCID 86614996, compound

Product 1

HCID 68815473(S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acid methyl esterYield 75.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Add (S)-2-sec-butylamino-6-chloroisonicotinic acid methyl ester (1.40 g, 5.75 mmol), 2-fluorophenylboronic acid (1.0 g, 7.15 mmol), tetrakis(triphenylphosphine)palladium (0) (0.664 g, 0.575 mmol), potassium carbonate (2.38 g, 17.3 mmol) and 1,4-dioxane (25 mL) to a sealed flask flushed with nitrogen. Heat and stir the mixture overnight and cool to room temperature. Filter the mixture through a filtering agent, concentrate and purify (silica gel chromatography, eluting with 4:96 ethyl acetate:hexanes) to give the title compound (1.31 g, 75%).

Workup

  1. customflushed with nitrogen
  2. temperatureHeat
  3. filtrationFilter the mixture through a filtering agent
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4:96 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-61167592ce754676a9278fb76d82d4ee
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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