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

HRID 1527655

반응식

HRID 1527655 반응식
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]

참가 물질

5

반응물 2

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

생성물 2

HCID 2409254-Methyl-2,6-dimethoxyphenol수율 10%HCID 27759582,5-Dimethoxy-4-methylphenol수율 5%

시약·촉매·용매 1

HCID 249755962,3,6-Trimethoxy-4-methylphenol용매

실험 절차

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.

후처리

  1. customresults in multiple reduction byproducts that

출처 및 근거

ORD 기록
ord-34cc4c7b15044dae8f35e923dbb7d348
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089605B2

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