Cesium carbonate → HCID 11540788, compound

HRID 1437447Notes

Reaction equation

HRID 1437447 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH2:15][CH2:16]Br)=[CH:9][C:8]=1[CH3:18])[CH3:2].[N:20]1[N:21]([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=2[OH:36])[N:22]=[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=12.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH2:15][CH2:16][O:36][C:30]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:29]=2[N:21]2[N:22]=[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]3=[N:20]2)=[CH:9][C:8]=1[CH3:18])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20446366HCID 20446366, compoundHCID 57941270HCID 57941270, compound

Product 1

HCID 11540788HCID 11540788, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of [4-(3-bromo-propylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (139 mg, 0.4 mmol) and 2-benzotriazole-2-yl-4-chloro-phenol (108 mg, 0.44 mmol) in MeCN (3 mL) was added Cs2CO3 (156 mg, 0.48 mmol). The mixture was stirred at room temperature for 4 hrs. The mixture was filtrated through Celite and washed with ethyl acetate. The solvent was evaporated and the residue was purified by flash chromatography on silica gel to give 145 mg of the desired ester.

Workup

  1. filtrationThe mixture was filtrated through Celite
  2. washwashed with ethyl acetate
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-59b6a5b0cdaf432c9c342c000d18fb5f
Source dataset
uspto-grants-2009_11
Patent number
US07622491B2

Reaction notes

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