Water → HCID 66633957, compound

HRID 536567Notes

Reaction equation

HRID 536567 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 107585Pentane, 3-(chloromethyl)-HCID 66634127HCID 66634127, compound

Product 1

HCID 66633957HCID 66633957, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester, 15. (0.2 g, 0.63 mmol) in DMF (5 mL) were added potassium carbonate 0.15 g (1.26 mmol), tetrabutylammonium iodide 0.03 g and 3-chloromethylpentane 0.15 g (1.26 mmol). The resulting mixture was heated at 150° C. in a microwave reactor. The mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to give 0.21 g (84%) of the methyl ester 16 as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-44dfa3922d5b4ebea2616507a9c0a11f
Source dataset
uspto-grants-2014_10
Patent number
US08859606B2

Reaction notes

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