Cesium carbonate → 2-(4-Chloro-phenyl)-1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-4-carboxylic acid ethyl ester

HRID 900241Notes

Reaction equation

HRID 900241 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]1[CH:30]=[C:29]([C:31]2[S:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[O:28][N:27]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:9]([CH2:25][C:26]2[CH:30]=[C:29]([C:31]3[S:32][C:33]([Cl:36])=[CH:34][CH:35]=3)[O:28][N:27]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 53440929ethyl 2-(4-chlorophenyl)-1H-imidazole-5-carboxylate

Product 1

HCID 691123712-(4-Chloro-phenyl)-1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (2.0 mmol) of 2-(4-Chlorophenyl)-3H-imidazole-4-carboxylic acid ethyl ester was dissolved in 5 ml of DMF and 2.6 g (8 mmol) of cesium carbonate were added at RT. After stirring for 15 min, 445 mg (1.6 mmol) of 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole were added. The reaction was stirred at room temperature for 16 h. The reaction solution was filtered and the product was purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). After lyophilization the product was obtained as a white solid. Yield: 480 mg; MS (LCMS-ES+): m/e=448.

Workup

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. filtrationThe reaction solution was filtered
  3. customthe product was purified by preparative RP-HPLC
  4. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)
  5. customAfter lyophilization the product was obtained as a white solid

Sources & evidence

ORD record
ord-101d6b3eb27642dfbee354d434412750
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

Loading…