Potassium Carbonate → HCID 69673476, Verbindung

HRID 1426284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426284
Cl[C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH:12](B(OCCCC)OCCCC)=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:3]1[C:2]([CH:12]=[CH2:13])=[N:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 27828122-Chloro-3-fluoropyridine-4-carboxylic acid

Produkt 1

HCID 69673476HCID 69673476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A solution of 2-chloro-3-fluoroisonicotinic acid (1.50 g, 8.55 mmol, Matrix), dibutyl vinylboronate (2.82 mL, 12.8 mmol, Aldrich), and potassium carbonate (1.42 g, 10.25 mmol) in N,N-dimethylacetamide (9 mL) and water (3 mL) was degassed by bubbling a stream of nitrogen through the solution for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51 mmol) was added and the mixture was similarly degassed for a further 10 minutes. The reaction vessel was sealed and heated in the microwave for 25 minutes at 135° C. The reaction mixture was filtered and purified using preparative HPLC (UV-detection) eluting with a gradient of H2O/MeCN containing 0.1% TFA. This reaction was run again on the same scale and the product of both runs were pooled. Solvent was removed from the eluent containing desired product in vacuo (1.3 g, 46%). 1H NMR (300 MHz, CD3OD): δ 8.45 (d, 1H), 7.69 (dd, 1H), 7.07 (ddd, 1H), 6.44 (dd, 1H), 5.65 (dd, 1H); 19F NMR (282 MHz, CD3OD): δ−129.64 (d, 1F); LCMS (M+H)+: 167.9.

Aufarbeitung

  1. customby bubbling a stream of nitrogen through the solution for 20 minutes
  2. customthe mixture was similarly degassed for a further 10 minutes
  3. customThe reaction vessel was sealed
  4. filtrationThe reaction mixture was filtered
  5. custompurified
  6. washeluting with a gradient of H2O/MeCN containing 0.1% TFA
  7. customSolvent was removed from the eluent
  8. additioncontaining desired product in vacuo (1.3 g, 46%)

Quellen und Nachweise

ORD-Eintrag
ord-30c3403d3e8c4a62bd1ecc003e7bea48
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

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