Water → HCID 86716132, Verbindung

HRID 627561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627561
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[C:21](Cl)[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]3[Cl:33])([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[OH:9])=[CH:4][CH:3]=1.[N:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[N:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.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:33][C:19]1[C:18]2[C:23](=[CH:24][CH:25]=[C:16]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[OH:9])[CH:17]=2)[N:22]=[C:21]([C:38]2[CH:39]=[N:34][CH:35]=[N:36][CH:37]=2)[C:20]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 74222811HCID 74222811, Verbindung

Produkt 1

HCID 86716132HCID 86716132, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (4-chlorophenyl)(2,4-dichloro-3-phenylquinolin-6-yl)(pyridin-3-yl)methanol (75 mg, 0.15 mmol, Example 17), pyrimidin-5-ylboronic acid (23 mg, 0.18 mmol), PdCl2(dppf) (11 mg, 0.015 mmol) and K2CO3 (42 mg, 0.30 mmol) in 10 mL dioxane was combined with 2 mL of water and heated to 70° C. After 3 hours, the reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified on an ISCO using 0-10% methanol in ethyl acetate and lyophilized to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ=9.06 (s, 1H), 8.64 (s, 2H), 8.60 (d, J=2.0 Hz, 1H), 8.57 (d, J=3.0 Hz, 1H), 8.35 (d, J=2.0 Hz, 1H), 8.17 (d, J=8.6 Hz, 1H), 7.69-7.78 (m, 2H), 7.27-7.42 (m, 8H), 7.19 (dd, J=6.3, 2.8 Hz, 2H); MS m/e 535.8 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on an ISCO

Quellen und Nachweise

ORD-Eintrag
ord-87e4bedca764479cb017a4b3c6fad288
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309222B2

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