Water → 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-iodo-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester

HRID 900234Notes

Reaction equation

HRID 900234 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([I:12])=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2].Br[CH2:14][C:15]1[CH:19]=[C:18]([C:20]2[S:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[O:17][N:16]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:14][C:15]2[CH:19]=[C:18]([C:20]3[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[O:17][N:16]=2)[C:8]([I:12])=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 178470396HCID 178470396, compound

Product 1

HCID 691122743-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-iodo-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg 2-Iodo-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester in 2 ml DMF 1.1 g caesium carbonate and 547 mg 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole [prepared by adopting a procedure described by Ewing, William R.; Becker, Michael R.; Choi-Sledeski, Yong Mi; Pauls, Heinz W.; He, Wei; Condon, Stephen M.; Davis, Roderick S.; Hanney, Barbara A.; Spada, Alfred P.; Burns, Christopher J.; Jiang, John Z.; Li, Aiwen; Myers, Michael R.; Lau, Wan F.; Poli, Gregory B; PCT Int. Appl. (2001), 460 pp. WO 0107436 A2] were added and the mixture was stirred for 2 h at RT. After addition of 5 ml water the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate and then concentrated under reduced pressure. The residue was directly subjected to the subsequent saponification reaction without further purification. Yield: 630 mg.

Workup

  1. filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was directly subjected to the subsequent saponification reaction without further purification

Sources & evidence

ORD record
ord-ea7c58355dfb4d118d7ba4d3b2469c0b
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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