Formaldehyde → HCID 86681910, compound

HRID 1749707Notes

Reaction equation

HRID 1749707 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[NH:22]1[CH2:32][CH2:31][CH2:30][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23]1.[CH2:33]=O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:33][N:22]4[CH2:32][CH2:31][CH2:30][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23]4)=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 98969Ethyl nipecotateHCID 1777704HCID 1777704, compound

Product 1

HCID 86681910HCID 86681910, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.10 g, 0.36 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with ethyl nipecotate (0.068 g, 0.43 mmol), and 37% aqueous formaldehyde (0.036 g, 0.46 mmol), and the mixture was stirred overnight at 80° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain ethyl (Z)-1-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperidine-3-carboxylate (0.056 g, 35%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-ca36dd1a57cf4e559987fa3cd879394b
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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