Water → HCID 86692416, compound

HRID 1748446Notes

Reaction equation

HRID 1748446 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].C([O:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][N:17]=2)[C:14]=1[CH3:15])=[O:9])C.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:1]([O:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[C:14]([CH3:15])=[C:10]([C:8]([OH:9])=[O:7])[CH:11]=[N:12]2)=[N:17][CH:18]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 86692417HCID 86692417, compound

Product 1

HCID 86692416HCID 86692416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Isopropylbromide (164 μl) was added to a suspension of 1-(5-hydroxypyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (333 mg) and potassium carbonate (558 mg) in N,N-dimethylformamide (1.5 ml) and stirred at 80° C. for 2.5 hours. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was reacted and treated in a similar manner as Reference Example 24(3) to give the titled compound (152 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was reacted

Sources & evidence

ORD record
ord-65a6d766180240a6bdfda9e5134ab393
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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