5-Ethoxymethoxy-benzofuran-2-boronic acid → AZD4694 Precursor

HRID 217215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217215
[C:1]([O:5][C:6](=[O:19])[N:7]([C:9]1[CH:14]=[CH:13][C:12](Br)=[C:11]([N+:16]([O-:18])=[O:17])[N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31](B(O)O)=[CH:30][C:29]=2[CH:36]=1)[CH3:21]>>[C:1]([O:5][C:6](=[O:19])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:31]2[O:32][C:28]3[CH:27]=[CH:26][C:25]([O:24][CH2:23][O:22][CH2:20][CH3:21])=[CH:36][C:29]=3[CH:30]=2)=[C:11]([N+:16]([O-:18])=[O:17])[N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 461839705-Ethoxymethoxy-benzofuran-2-boronic acidHCID 46183971(5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 46183972AZD4694 PrecursorAusbeute 90,2 %

Versuchsvorschrift

By following the same procedure as described in Example 1 (step d), was prepared using (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester (12) (100 mg, 0.30 mmol) and 5-ethoxymethoxy-benzofuran-2-boronic acid (4) (92.5 mg, 0.39 mmol). Work-up as described in example 1d, followed by purification of the crude product by flash column chromatography using 10-25% ethyl acetate in hexane. Evaporation of solvent afforded 120 mg of the desired compound (13) as yellowish solid.

Aufarbeitung

  1. customwas prepared
  2. customfollowed by purification of the crude product by flash column chromatography
  3. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-eba754db6f7646e29e200a07ef6c35d6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193363B2

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