APE1/Ref-1 Redox Inhibitor APX3330 → 4-Methyl-2,6-dimethoxyphenol

HRID 1527655

反応式

HRID 1527655 の反応式
CCCCCCCCC/C(/C(O)=O)=C\[C:12]1[C:18](=[O:19])[C:17]([O:20]C)=[C:16]([O:22][CH3:23])[C:14](=O)[C:13]=1[CH3:24].Br[C:29]1C(Br)=C(C)C=C(Br)[C:30]=1[OH:38]>CC1C=C(OC)C(O)=C(OC)C=1OC>[CH3:23][O:22][C:16]1[CH:14]=[C:13]([CH3:24])[CH:12]=[C:18]([O:19][CH3:29])[C:17]=1[OH:20].[CH3:23][O:22][C:16]1[CH:14]=[C:13]([CH3:24])[C:12]([O:38][CH3:30])=[CH:18][C:17]=1[OH:20]

参加物

5

反応物 2

HCID 6439397APE1/Ref-1 Redox Inhibitor APX3330HCID 126005252,3,6-Tribromo-4-methylphenol

生成物 2

HCID 2409254-Methyl-2,6-dimethoxyphenol収率 10%HCID 27759582,5-Dimethoxy-4-methylphenol収率 5%

試薬・触媒・溶媒 1

HCID 249755962,3,6-Trimethoxy-4-methylphenol溶媒

実験手順

The second step in the synthesis of E3330 is the most problematic, where the Ullmann-type methanolysis of 2,3,6-tribromo-4-methylphenol (5) results in multiple reduction byproducts that are not disclosed in the literature.13,14 The optimized Ullmann conditions in our hands result in a mixture of 4-methyl-2,3,6-trimethoxyphenol (11, 75-85%), 2,6-dimethoxy-4-methylphenol (12, 10-15%), and 2,5-dimethoxy-4-methylphenol (13, 5-10%). (Scheme 2) The resulting phenols are alkylated to generate 2,3,4,5-tetramethoxytoluene (6) and the two trimethoxytoluenes (14 and 15). The isolated yield is considerably lower than the observed conversion by NMR, and removal of the two reaction sideproducts is necessary because both lead to E3330 derivatives missing crucial methoxy substituents.

後処理

  1. customresults in multiple reduction byproducts that

出典と根拠

ORDレコード
ord-34cc4c7b15044dae8f35e923dbb7d348
出典データセット
uspto-grants-2015_07
特許番号
US09089605B2

関連ノート

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