Formaldehyde → HCID 86681914, compound

HRID 1749716Notes

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])[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].[CH2:41]=O>CO>[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]([CH2:41][N:38]4[CH2:39][CH2:40][N:35]([C:33]([O:32][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:34])[CH2:36][CH2:37]4)=[C:19]([OH:21])[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-5-phenylbenzofuran-3(2H)-one (0.035 g, 0.10 mmol) in methanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.021 g, 0.11 mmol), and 37% aqueous formaldehyde (0.011 g, 0.15 mmol), and the mixture was stirred overnight at 40° C. 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-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-5-phenyl-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.031 g, 56%).

Workup

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

Sources & evidence

ORD record: ord-db76faffc0194a8795cd47ee3aa6f2c7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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