Potassium Phosphate, Tribasic → HCID 86728224, Verbindung

HRID 1776794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776794
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.C(OC([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1B(O)O)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:4]1[N:3]=[C:2]([C:19]2[NH:18][C:26]3[C:21]([CH:20]=2)=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 717433362,6-Dichloro-3-methoxypyridine

Produkt 1

HCID 86728224HCID 86728224, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a degassed solution of compound 2,6-dichloro-3-methoxypyridine (8.9 g, 0.05 mol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (13 g, 0.05 mol) and K3PO4 (31.8 g, 3.0 mol) in DMF (100 mL) was added Pd(dppf)Cl2 (3.65 g, 5 mmol) under N2. The mixture was heated at 60° C. for about 15 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide the desired product of 2-(6-chloro-3-methoxypyridin-2-yl)-1H-indole (9.0 g, yield: 69.8%). 1H-NMR (CDCl3, 400 MHz) δ 9.52 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.38˜7.43 (m, 2H), 7.07˜7.26 (m, 4H), 4.03 (s, 3H). MS (M+H)+: 259/261.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter being concentrated in vacuo
  6. customthe resulting resulting residue
  7. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-3f9a02eb11a747078ca15bfd777101a4
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265773B2

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