Diethyl Malonate → HCID 14293036, compound

HRID 1017718Notes

Reaction equation

HRID 1017718 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[NH:8][C:9](=[O:15])OC(C)(C)C)=O.C(OCC)(=O)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].N1CCCCC1>CCO>[O:15]=[C:9]1[NH:8][C:4]2[S:5][CH:6]=[CH:7][C:3]=2[CH:1]=[C:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 18404088HCID 18404088, compound

Product 1

HCID 14293036HCID 14293036, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-formyl-2-thienylcarbamate (11-3, 1.90, 8.36 mmol, 1 equiv), diethyl malonate (2.54 mL, 16.7 mmol, 2.00 equiv), and piperidine (0.413 mL, 4.18 mmol, 0.500 equiv) in EtOH (100 mL) was heated at reflux for 6 h. The reaction mixture was concentrated, and the residue was purified by flash column chromatography (EtOAc, initally, then 10% MeOH in EtOAc) to give ethyl 6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (10-4). 1H NMR (400 MHz, CDCl3) δ 11.57 (brs, 1H), 8.60 (s, 1H), 7.33 (d, 1H, J=6.0 Hz), 7.21 (d, 1H, J=6.0 Hz), 4.49 (q, 2H, J=7.1 Hz), 1.46 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureat reflux for 6 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash column chromatography (EtOAc

Sources & evidence

ORD record
ord-d79d17f1b85642d8b36f31850bd51279
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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