Ethanol → HCID 86726878, compound

HRID 924420Notes

Reaction equation

HRID 924420 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[N:24]=[C:23](Br)[CH:22]=[CH:21][C:18]=1[CH:19]=O.N1CCCC1.[CH3:31][CH2:32][OH:33]>>[NH2:1][C:8]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:16][C:17]2[C:18]([CH:19]=1)=[CH:21][CH:22]=[C:23]([O:33][CH2:32][CH3:31])[N:24]=2

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 1049Pyridine2×HCID 31268PyrrolidineHCID 66144Ethyl bromopyruvateHCID 722125982-Amino-6-bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86726878HCID 86726878, compound

Procedure

A solution of pyridine (0.13 mL, 1.6 mmol) and ethyl bromopyruvate (0.22 mL, 1.7 mmol) in EtOH (0.5 mL) was stirred at 70° C. in a sealed vial for 16 h. The reaction mixture was allowed to cool to ambient temperature and a solution of 2-amino-6-bromonicotinaldehyde (317 mg, 1.58 mmol) and pyridine (0.76 mL, 9.5 mmol) in EtOH (1 mL) was added. The reaction mixture then was heated at 100° C. in a sealed vial for 16 h. Pyrrolidine (0.26 mL, 3.2 mmol) was added, and stirring in the sealed vial was continued at 100° C. i for 16 h. The crude reaction mixture was purified by flash chromatography (40 g silica gel column, eluting with 0-100% EtOAc/hexanes) to afford the sub-title compound. LCMS (ESI) calc. for C13H16N3O3 [M+H]+: m/z=262.1. found: 262.0.

Workup

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

Sources & evidence

ORD record
ord-0cc41acc01694846b84a176fd056cb2b
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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