Cesium carbonate → {6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

HRID 490766Notes

Reaction equation

HRID 490766 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH:18]([CH3:20])[CH3:19].C([O:23][C:24](=[O:36])[CH2:25][C:26]1[C:27]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:28]=2[S:29][CH:30]=1)C.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>C(#N)C.C(O)C>[CH:18]([C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:7][C:3]=1[CH2:2][O:35][C:32]1[CH:33]=[CH:34][C:27]2[C:26]([CH2:25][C:24]([OH:36])=[O:23])=[CH:30][S:29][C:28]=2[CH:31]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterHCID 589340885-Chloromethyl-4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole

Product 1

HCID 10368353{6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloromethyl-4-isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole (100 mg, 0.31 mmol) and (6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (75 mg, 0.31 mmol) in acetonitrile (3 mL) is added Cs2CO3 (200 mg, 0.62 mmol). The mixture is stirred at room temperature overnight, ethanol (1 mL) is added, followed by NaOH (5 N, 1.0 mL). The mixture is heated at 50° C. for 2 hrs, solvent is evaporate, the residue is diluted with water, acidified by 5N HCl and extracted with ethyl acetate. Concentration and reversed phase HPLC purification yields the title product. MS (ES): 490.0 (M+−1).

Workup

  1. temperatureThe mixture is heated at 50° C. for 2 hrs
  2. customsolvent is evaporate
  3. additionthe residue is diluted with water
  4. extractionextracted with ethyl acetate
  5. concentrationConcentration
  6. customphase HPLC purification

Sources & evidence

ORD record
ord-693ccb0ba6414c359f00c99c86af5c81
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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