Formaldehyde → HCID 86681939, compound

HRID 1749744Notes

Reaction equation

HRID 1749744 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[CH2:36]=O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:36][N:33]3[CH2:34][CH2:35][N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:29])[CH2:31][CH2:32]3)=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 44554577HCID 44554577, compound

Product 1

HCID 86681939HCID 86681939, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (Z)-2-[(5-bromo-1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.30 g, 0.84 mmol) in ethanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.17 g, 0.93 mmol), and 37% aqueous formaldehyde (0.093 g, 1.1 mmol), and the mixture was stirred overnight at 50° 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 tert-butyl (Z)-4-({2-[(5-bromo-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}-methyl)piperazine-1-carboxylate (0.15 g, 33%).

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-9da3361f00d24e6b835ea9e27100dc83
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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