Water → tert-butyl N-(4-fluoropyridin-2-yl)carbamate

HRID 626931

Reaktionsgleichung

Reaktionsgleichung von HRID 626931
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][N:3]=1.[C:9](=[O:16])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[NH2:10].[OH-].[Na+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:10][C:9](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 77922tert-Butyl carbamateHCID 27827922-Chloro-4-fluoropyridine

Produkt 1

HCID 51354888tert-butyl N-(4-fluoropyridin-2-yl)carbamateAusbeute 128,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Palladium (II) acetate (1.69 g, 7.53 mmol) and Xantphos (8.71 g, 15.05 mmol) were dissolved/suspended in degassed 1,4-dioxane (1200 mL) in a nitrogen atmosphere. 2-Chloro-4-fluoropyridine (99 g, 753 mmol) and tert-butyl carbamate (97 g, 828 mmol) in 1,4-dioxane (550 mL) were added, followed by sodium hydroxide (45.2 g, 1.12 mol) and water (20 mL). The resulting mixture was heated at 100° C. for 2 h. The mixture was cooled to ambient temperature and filtered over celite. The residue was washed with 1,4-dioxane and the filtrate was concentrated to afford a yellow solid (206 g). The crude material was recrystallized from 2-propanol (400 mL) and dried to afford the title compound (120.8 g) as a white solid. LCMS 213 [M+H], RT 1.96 minutes, purity 94%.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered over celite
  3. washThe residue was washed with 1,4-dioxane
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f1c130313d444180b5c320f703a122dd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309243B2

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