Potassium Phosphate, Tribasic → HCID 67208623, Verbindung

HRID 711241

Reaktionsgleichung

Reaktionsgleichung von HRID 711241
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14][N:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)CC>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[CH:6][N:7]=2)[CH:15]=[CH:14][N:13]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acid

Produkt 1

HCID 67208623HCID 67208623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6568(+-)-2-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a flask containing (6-chloropyridin-3-yl)methanamine 33-2 (375 mg, 2.63 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid 33-1 (500 mg, 2.63 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (124 mg, 0.30 mmol) and potassium phosphate (1.90 g, 9.00 mmol) under argon was added 2-butanol (4 mL). The mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the mixture was filtered through celite cake. The filtrate was diluted with ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 33-3 as a yellow solid. MS m/z 254.1 (M+1)

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite cake
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol containing ˜7N ammonia in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3bcf7431285b4be586bd389a0b629ac8
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181235B2

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