Water → (2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

HRID 1161541노트

반응식

HRID 1161541 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[CH3:18][O:19][C:20](=[O:45])[N:21]=[C:22]([S:43][CH3:44])[C:23](=[N:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=1)[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([OH:32])[C:25]=1[F:33].O>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:19][C:20](=[O:45])[N:21]=[C:22]([S:43][CH3:44])[C:23]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:25]=1[F:33])=[N:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 72312839[2-(4-Cyanophenylimino)-2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester

생성물 1

HCID 72312754(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester수율 77.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

After adding 1.8 g of potassium carbonate and 3 g of (2-bromoethoxy)-t-butyldimethylsilane to a solution of 3.45 g of [2-(4-cyanophenylimino)-2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (163b)) in 10 ml of DMF, the mixture was stirred at 50° C. for 5 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (3.73 g, isomeric mixture) as a light yellow solid.

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

출처 및 근거

ORD 기록
ord-d5fa8e59c2774addafc3707c8c0e4e7a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

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