Water → 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2375810Notes

Reaction equation

HRID 2375810 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:14])=[C:9]([CH:12]=[O:13])[C:10]=1[CH3:11])=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]1[CH:27]=[C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)[O:25][N:24]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:27]=[C:26]([C:28]3[S:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[O:25][N:24]=2)[C:8]([CH3:14])=[C:9]([CH:12]=[O:13])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1374862199-64-6HCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole

Product 1

HCID 867607851-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.60 g) in DMF (26 mL) was added Cs2CO3 (6.51 g). The mixture was stirred for 30 min at RT, then 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (3.71 g) was added. Stirring was continued for 2 h at RT. Water was added and the phases were separated. The aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried (MgSO4) and was concentrated under reduced pressure to give crude 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (4.20 g), which was directly used in the next step without further purification.

Workup

  1. stirringStirring
  2. waitwas continued for 2 h at RT
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-75bdf43e893448c786d5b677eab2d798
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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