Potassium Carbonate → HCID 71621141, Verbindung

HRID 1473888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473888
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N:18]2[CH3:23].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[N:17][N:18]3[CH3:23])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 866907154-(chloromethyl)-1-methyl-1H-indazole

Produkt 1

HCID 71621141HCID 71621141, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-5-methoxybenzaldehyde (170 mg, 1.12 mmol), 4-(chloromethyl)-1-methyl-1H-indazole (1.12 mmol), and K2CO3 (618 mg, 4.48 mmol) was reflux in CH3CN (20 mL) for 2 h. The mixture was filtered and the solid was washed with DCM. The filtrate was concentrated and purified on silica gel using a mixture of EtOAc and MeOH as eluent to give 5-methoxy-2-((1-methyl-1H-indazol-4-yl)methoxy)benzaldehyde (215 mg, 81% for three steps) as a white solid. 1H NMR (400 MHz; DMSO) δ=10.39 (s, 1H), 8.20 (d, 1H), 7.63 (d, 1H) 7.36-7.64 (m, 2H), 7.23-7.29 (m, 2H), 7.18 (d, 1H), 5.58 (s, 2H), 4.06 (s, 3H), 3.34 (s, 3H). LRMS (M+H+) m/z 297.1.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified on silica gel using
  5. additiona mixture of EtOAc and MeOH as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1149250aa3644a6e963713b7f1ff0bd4
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018210B2

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