Potassium Fluoride → HCID 90418179, compound

HRID 923693Notes

Reaction equation

HRID 923693 reaction equation
[F-].[K+].[Cl:3][C:4]1[C:12]2[O:11][CH:10]=[CH:9][C:8]=2[C:7](B2OCC(C)(C)CO2)=[CH:6][CH:5]=1.O.O.O.O.P(C1C=C(S([O-])(=O)=O)C=CC=1)(C1C=C(S([O-])(=O)=O)C=CC=1)C1C=C(S([O-])(=O)=O)C=CC=1.[Na+].[Na+].[Na+].[NH2:59][C:60]1[C:65]([F:66])=[C:64](Cl)[N:63]=[C:62]([C:68]([O:70][CH3:71])=[O:69])[C:61]=1[Cl:72]>C(O[Pd]OC(=O)C)(=O)C.O.C(OCC)(=O)C.C(#N)C>[NH2:59][C:60]1[C:65]([F:66])=[C:64]([C:7]2[C:8]3[CH:9]=[CH:10][O:11][C:12]=3[C:4]([Cl:3])=[CH:5][CH:6]=2)[N:63]=[C:62]([C:68]([O:70][CH3:71])=[O:69])[C:61]=1[Cl:72]

Participants

9

Reactant 4

HCID 522689Potassium FluorideHCID 19688780HCID 19688780, compoundHCID 22677265Methyl 4-amino-3,6-dichloro-5-fluoropicolinateHCID 90417382HCID 90417382, compound

Product 1

HCID 90418179HCID 90418179, compoundYield 17.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combined potassium fluoride (0.365 g, 6.28 mmol), diacetoxypalladium (0.047 g, 0.209 mmol), and 2-(7-chlorobenzofuran-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane (0.609 g, 2.301 mmol), sodium 3,3′,3″-phosphinetriyltribenzenesulfonate tetrahydrate (0.134 g, 0.209 mmol), methyl 4-amino-3,6-dichloro-5-fluoropicolinate (0.5 g, 2.092 mmol). Added water (3 mL) and acetonitrile (1 mL). Heated reaction mixture at 150° C. in a microwave reactor for 6 minutes. Diluted cooled reaction mixture with ethyl acetate and water and filtered through cotton plug. Dried organic phase (Na2SO4) and concentrated under vacuum. Purified by reverse phase chromatography to provide the title compound as a white solid (127 mg, 12.5% yield).

Workup

  1. temperatureHeated
  2. customreaction mixture at 150° C. in a microwave reactor for 6 minutes
  3. additionDiluted
  4. temperaturecooled
  5. filtrationfiltered through cotton plug
  6. concentrationDried organic phase (Na2SO4) and concentrated under vacuum
  7. customPurified by reverse phase chromatography

Sources & evidence

ORD record
ord-84679aa1f84144db88999cf89779edb9
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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