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6-Methyl-2-(4-methylene-1-piperidyl)-3-nitropyridine → 3-[(6-Methylpyridin-2-yl)ethynyl]-8-pyridin-2-yl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carbonitrile

HRID 2040874
Notes
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Reaction equation

HRID 2040874 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](N2CCC(=C)CC2)[C:5]([N+]([O-])=O)=[CH:4][CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1([C:40]#[N:41])[CH2:39][CH2:38][C:27]2([CH2:31][C:30]([C:32]#[C:33][Si](C)(C)C)=[N:29][O:28]2)[CH2:26][CH2:25]1>>[CH3:1][C:2]1[N:7]=[C:6]([C:33]#[C:32][C:30]2[CH2:31][C:27]3([CH2:38][CH2:39][C:24]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)([C:40]#[N:41])[CH2:25][CH2:26]3)[O:28][N:29]=2)[CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 574938106-Methyl-2-(4-methylene-1-piperidyl)-3-nitropyridineHCID 574938468-(2-Pyridyl)-2-(2-trimethylsilylethynyl)-4-oxa-3-azaspiro[4.5]dec-2-ene-8-carbonitrile

Product 1

HCID 566436093-[(6-Methylpyridin-2-yl)ethynyl]-8-pyridin-2-yl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carbonitrile

Procedure

The title compound was prepared following the method described for the compound of Example 3, replacing Compound 3c with Compound 48b. The crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum ether-EtOAc from 65:35 to 4:6) to give the title compound as yellow oil. Yield: 43.4%.

Workup

  • customThe title compound was prepared
  • customThe crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum ether-EtOAc from 65:35 to 4:6)
  • Sources & evidence

    ORD record
    ord-f1a935ea5dab4695a47b79b53d0c3c42
    Source dataset
    uspto-grants-2013_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08580962B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes