2-Amino-4-fluoropyridine → N-(4-fluoropyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 928304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928304
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=2)[O:3]1.[NH2:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][N:21]=1>C(#N)C>[F:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([NH:19][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([B:4]3[O:3][C:2]([CH3:18])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]3)=[CH:10][CH:11]=2)[CH:25]=1

Komponenten

4

Edukt 2

HCID 183278082-Amino-4-fluoropyridineHCID 579816664-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride

Produkt 1

HCID 71222688N-(4-fluoropyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride (1.688 mmol, 450 mg) in acetonitrile (24.8 mL) was added 2-amino-4-fluoropyridine (4.22 mmol, 473 mg). The reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated to a small volume, 3% aq. citric acid solution (18 mL) was added and the mixture was extracted with dichloromethane (2×15 mL). The combined organic layer was washed with 3% aq. citric acid solution, dried over magnesium sulfate, filtered and evaporated to afford 542.2 mg of N-(4-fluoropyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (94%) as an off-white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to a small volume, 3% aq. citric acid solution (18 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (2×15 mL)
  4. washThe combined organic layer was washed with 3% aq. citric acid solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4cab51ebe3e24e50805575196fb308f6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290504B2

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