Water → HCID 66633957, compound

HRID 1053987Notes

Reaction equation

HRID 1053987 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-e9eaf5e0a032475cbcf0488c908f5a45
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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