Formaldehyde → HCID 71278577, compound

HRID 1749699Notes

Reaction equation

HRID 1749699 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.[CH3:22][N:23]([CH3:29])[CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1.[CH2:30]=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]([CH2:30][N:26]4[CH2:27][CH2:28][CH:24]([N:23]([CH3:29])[CH3:22])[CH2:25]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 1777704HCID 1777704, compoundHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 71278577HCID 71278577, compoundYield 21%

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 (0.050 g, 0.18 mmol) obtained in Example A1, Step 1 in ethanol (3.0 mL) was added with 3-(dimethylamino)pyrrolidine (0.025 g, 0.22 mmol), and 37% aqueous formaldehyde (0.020 g, 0.24 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 (Z)-2-[(1H-indol-3-yl)methylene]-7-{[3-(dimethylamino)pyrrolidin-1-yl]methyl}-6-hydroxybenzofuran-3(2H)-one (0.015 g, 21%).

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-153bab68fdca48859acb0d509f378bfb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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