Potassium Carbonate → HCID 59830914, compound

HRID 1472280Notes

Reaction equation

HRID 1472280 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:18][C:19]([C:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[NH:23][N:22]=1)=[O:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+].[Li+].[Cl-]>CN(C=O)C>[CH2:16]([O:18][C:19]([C:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[N:23]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])=[CH:8][CH:9]=2)[N:22]=1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 7365260ethyl 3-propyl-1H-pyrazole-5-carboxylateHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 59830914HCID 59830914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the recovered intermediate (19a) (1.4 g, 5 mmol, 1.0 eq) dissolved into 15 mL DMF, was added 5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (910 mg, 5.0 mmol, 1.0 eq) and potassium carbonate (0.8 g, 5.5 mmol, 1.1 eq) and the mixture was stirred at room temperature for 16 hours. The mixture was then added to 50 mL of 10% aq. LiCl solution and extracted with 50 mL EtOAc. The organic was dried over MgSO4, and concentrated under reduced pressure to yield intermediate (19b) and its regioisomer in a 1:1 ratio. The recovered regioisomers were dissolved into 25 mL MeOH. To this was added 10 mL of 1M NaOH and the mixture was stirred at room temperature over night.

Workup

  1. extractionextracted with 50 mL EtOAc
  2. dry with materialThe organic was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60e85cd7aeeb41c7bf14cea361b6bc05
Source dataset
uspto-grants-2015_04
Patent number
US09012485B2

Reaction notes

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