(4-Cyano-3-fluorophenyl)boronic acid → HCID 58504784, Verbindung

HRID 2367319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367319
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]2[C:14]([NH2:16])=[O:15])[CH:5]=[C:4](Cl)[N:3]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[F:29])#[N:19]>O1CCOCC1.C([O-])(O)=O.[Na+].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>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]2[C:14]([NH2:16])=[O:15])[CH:5]=[C:4]([C:23]2[CH:24]=[CH:25][C:20]([C:18]#[N:19])=[C:21]([F:29])[CH:22]=2)[N:3]=1

Komponenten

6

Edukt 2

HCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 585045274-(2-Amino-6-chloro-4-pyrimidinyl)-3-morpholinecarboxamide

Produkt 1

HCID 58504784HCID 58504784, VerbindungAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 4-(2-amino-6-chloro-4-pyrimidinyl)-3-morpholinecarboxamide (390 mg, 1.51 mmol), Pd(PPh3)4 (91 mg, 0.08 mmol), and (4-cyano-3-fluorophenyl)boronic acid (285 mg, 1.73 mmol) in 1,4-dioxane (6 mL) and saturated aqueous NaHCO3 (2 mL) was stirred at 95° C. under argon in a sealed tube for 18 hours. The mixture was cooled, quenched with saturated aqueous NaHCO3 (25 mL) and extracted with EtOAc (3×25 mL). The extracts were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (34 g, SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (360 mg) as a white solid. LC-MS (ES) m/z=343 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customquenched with saturated aqueous NaHCO3 (25 mL)
  3. extractionextracted with EtOAc (3×25 mL)
  4. washThe extracts were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (34 g, SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient)

Quellen und Nachweise

ORD-Eintrag
ord-cc5cc8f4b3bd4fbca396bbe66824033a
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

Notizen zur Reaktion

Wird geladen…