Water → HCID 60209930, Verbindung

HRID 1497338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497338
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1.O>C1COCC1.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].C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179484394-(Chloromethyl)-2-methoxypyridineHCID 60209927HCID 60209927, Verbindung

Produkt 1

HCID 60209930HCID 60209930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of methyl 8-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-2-carboxylate (S1) (130 mg, 0.393 mmol), Cs2CO3 (384 mg, 1.178 mmol), PdCl2(dppf)-CH2Cl2 adduct (32.1 mg, 0.039 mmol) in a microwave tube were added a solution of 4-(chloromethyl)-2-methoxypyridine (124 mg, 0.785 mmol) in THF (3 mL) followed by adding water (0.3 mL). The mixture was heated at 100° C. for 1 h. The reaction was cooled and diluted with EtOAc. The bottom H2O layer was removed. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA) to give methyl 8-fluoro-4-[(2-methoxypyridin-4-yl)methyl]quinoline-2-carboxylate (V4). ES-MS [M+1]+: 327.2.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customThe bottom H2O layer was removed
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-02a5903297c2408e8e69cd5d00a58633
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199939B2

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