Acetic Acid → HCID 68554750, compound

HRID 1869195Notes

Reaction equation

HRID 1869195 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[CH:2]1.[C:12]([O:18][CH2:19]C(C)(C)C)(=[O:17])[CH2:13][C:14]([O-:16])=[O:15].N1[CH2:29][CH2:28][CH2:27]CC1.[C:30](O)(=O)C>C(#N)C>[CH3:19][O:18][C:12](=[O:17])[C:13](=[CH:10][C:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[NH:1][CH:2]=1)[C:14]([O:16][C:28]([CH3:27])([CH3:29])[CH3:30])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 179641321H-Pyrrolo[3,2-b]pyridine-3-carbaldehydeHCID 71651205HCID 71651205, compound

Product 1

HCID 68554750HCID 68554750, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1H-pyrrolo[3,2-b]pyridin-3-carbaldehyde (660 mg, 4.5 mmol), tert-butyl-methyl malonate (3.8 mL, 22.5 mmol), piperidine (0.12 mL) and acetic acid (0.12 mL) in acetonitrile (40 mL) was heated to reflux. The resulting mixture was stirred at RT for 24 h, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 2-(1H-Pyrrolo[3,2-b]pyridin-3-yl-methylene)-malonic acid tert-butyl ester methyl ester as a mixture of cis- and trans-isomers (780 mg, 57% yield).

Workup

  1. temperaturewas heated to reflux
  2. concentrationconcentrated
  3. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-c5faf3a4d39840868a7d0ff3e00b7152
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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