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

HRID 1161534Notes

Reaction equation

HRID 1161534 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[CH3:19][O:20][C:21](=[O:50])[N:22]=[C:23]([S:48][CH3:49])[C:24]([C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([OH:46])[C:39]=1[F:47])=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH3:37])[O:34][N:33]=2)=[CH:28][CH:27]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:20][C:21](=[O:50])[N:22]=[C:23]([S:48][CH3:49])[C:24]([C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:39]=1[F:47])=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH3:37])[O:34][N:33]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 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 72312847(2-{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-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 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 313 mg of cesium carbonate and 0.257 ml of (3-bromopropoxy)-t-butyldimethylsilane to a solution of 339 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)) in 8 ml of DMF, the mixture was stirred at room temperature for 15 hours. Next, 100 ml of water was added to the reaction mixture and extraction was performed with 300 ml of ethyl acetate. The organic layer was washed with 50 ml of water and 50 ml of saturated brine in that order and then 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 (ethyl acetate-heptane) to give the title compound (413 mg).

Workup

  1. washThe organic layer was washed with 50 ml of water and 50 ml of saturated brine in that order
  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 (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-fd1d53eaad59487a99d74ef33462534a
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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