Potassium Carbonate → (2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester

HRID 1161564Notes

Reaction equation

HRID 1161564 reaction equation
[CH3:1][O:2][C:3](=[O:32])[N:4]=[C:5]([S:30][CH3:31])[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([OH:28])[C:21]=1[F:29])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44].[Cl-].[NH4+]>O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:32])[N:4]=[C:5]([S:30][CH3:31])[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:21]=1[F:29])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 72312745[2-(2-Fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

Product 1

HCID 72312769(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 15 ml of a DMF solution containing 522 mg of [2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (3d)), 173 mg of potassium carbonate and 0.269 ml of (2-bromoethoxy)-t-butyldimethylsilane were added. The resulting mixture was stirred at room temperature for 15 hours, and then 25 ml of water and 25 ml of saturated ammonium chloride aqueous solution were added thereto. The mixture was extracted with 150 ml of ethyl acetate. The organic layer was washed with 50 ml of water and then with 50 ml of saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (210 mg).

Workup

  1. additionwere added
  2. extractionThe mixture was extracted with 150 ml of ethyl acetate
  3. washThe organic layer was washed with 50 ml of water
  4. dry with materialwith 50 ml of saturated brine and dried over anhydrous magnesium sulfate
  5. customThe desiccating agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-e67d6474b4c647d89b87ca430269ccc0
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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