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

HRID 1161541Notes

Reaction equation

HRID 1161541 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d5fa8e59c2774addafc3707c8c0e4e7a
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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