Water → HCID 58066674, compound

HRID 390408Notes

Reaction equation

HRID 390408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13]Br)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:15]#[N:16].[K+].O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13][C:15]#[N:16])[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 58066672tert-butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 58066674HCID 58066674, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 4-bromomethyl-pyrazole-1-carboxylic acid tert-butyl ester (1.0 g, 3.5 mmol) in DMSO (25 mL) was added potassium cyanide (0.228 g, 3.5 mmol), and the reaction was stirred for 15 minutes at room temperature. The mixture was poured into H2O and extracted with EtOAc. The combined organic layers were dried and concentrated to give the title compound, along with some starting material and the unbrominated starting material from the previous step. The material was dissolved in DMSO (10 mL), and potassium cyanide (0.100 g, 1.5 mmol) was added. The reaction was stirred for 1 hour at room temperature, and then worked-up, dried, and concentrated to give the title compound, contaminated with a small amount of 4-methyl-pyrazole-1-carboxylic acid tert-butyl ester.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-07afd10bac76446f830f27097ab0f634
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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