Nitrogen → 2-(4-Bromo-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

HRID 1189390Notes

Reaction equation

HRID 1189390 reaction equation
N#N.C([O-])([O-])=O.[K+].[K+].[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:19]OS(C)(=O)=O)[O:17][CH:18]=1)=[O:13])[CH3:10].[Br:25][C:26]1[CH:27]=[N:28][NH:29][CH:30]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC(C)=O>[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:19][N:28]2[CH:27]=[C:26]([Br:25])[CH:30]=[N:29]2)[O:17][CH:18]=1)=[O:13])[CH3:10]

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 86664911HCID 86664911, compound

Product 1

HCID 671284292-(4-Bromo-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), K2CO3 (356 mg, 2.55 mmol) was added at rt to a solution of 2-methanesulfonyloxymethyl-oxazole-4-carboxylic acid ethyl ester (127 mg, 0.51 mmol), TBAB (33 mg, 0.10 mmol) and 4-bromo-1H-pyrazole (76 mg, 0.51 mmol) in acetone (5.0 mL). After stirring at rt for 2 h, the solvent was removed under reduced pressure. The residue was partitioned between water and EA, the two layers were separated and the aq. layer was extracted twice with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as an orange solid. TLC: rf (1:1 hept-EA)=0.27. LC-MS-conditions 01: tR=0.84 min, [M+H]+=299.96.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water and EA
  3. customthe two layers were separated
  4. extractionthe aq. layer was extracted twice with EA
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b73c348886d34503abe221913ef0de69
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…