Pyridine → HCID 86726882, compound

HRID 924431Notes

Reaction equation

HRID 924431 reaction equation
[N:1]1C=CC=CC=1.Br[CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[NH2:16][C:17]1[C:22]([CH:23]=O)=[CH:21][N:20]=[C:19]([Br:25])[CH:18]=1.N1CCCC1>CCO>[NH2:1][C:8]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][N:20]=[C:19]([Br:25])[CH:18]=2

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 31268PyrrolidineHCID 66144Ethyl bromopyruvateHCID 72212268HCID 72212268, compound

Product 1

HCID 86726882HCID 86726882, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of pyridine (0.11 mL, 1.4 mmol) and ethyl bromopyruvate (0.19 mL, 1.5 mmol) in EtOH (2.2 mL) was stirred at 70° C. in a sealed vial for 16 h. The reaction mixture was allowed to cool to ambient temperature prior and a solution of 4-amino-6-bromonicotinaldehyde (0.278 g, 1.38 mmol) and pyridine (0.67 mL, 8.3 mmol) in EtOH (1 mL) was then added. The resulting mixture was heated at 100° C. in a sealed vial for 16 h. Stirring was continued at 100° C. for an additional 24 h. Pyrrolidine (0.23 mL, 2.8 mmol) was added and stirring was continued at 100° C. for 5 h in a sealed vial. The crude reaction mixture was purified by flash chromatography (40 g silica gel column, eluting with 0-100% EtOAc/hexanes) to give the sub-title compound. LCMS (ESI) calc. for C11H11BrN3O2 [M+H]+: m/z=296.0. found: 295.9.

Workup

  1. temperatureThe resulting mixture was heated at 100° C. in a sealed vial for 16 h
  2. stirringstirring
  3. waitwas continued at 100° C. for 5 h
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography (40 g silica gel column, eluting with 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0ff415884a4742558900ec61825144d6
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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