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

HRID 627315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627315
[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-24b15600b7da44a9ae29832921a68569
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309267B2

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