Ethyl Acetate → HCID 66673555, compound

HRID 251796Notes

Reaction equation

HRID 251796 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH:9]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:10]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 66673555HCID 66673555, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-fluoropyridine (1.76 mg, 10 mmol) and 3.62 g (10 mmol) of tert-butyl pyrrolidin-3-ylcarbamate were dissolved in 20 ml of N,N-dimethylformamide. Potassium carbonate (1.38 g, 10 mmol) was added to the solution, and the mixture was stirred at 100° C. for 6 hr. Ethyl acetate (60 ml) and 8.5 ml of water were added to the reaction solution, and the organic layer was washed five times with 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and was filtered. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give 1.23 g (yield 36%) of the title compound.

Workup

  1. washthe organic layer was washed five times with 30 ml of water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationwas filtered
  4. customThe solvent was then removed by distillation
  5. customthe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d2fca95e96044d369ede5be188ff12be
Source dataset
uspto-grants-2011_01
Patent number
US07867980B2

Reaction notes

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