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 2040874Notes

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

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

  1. customThe title compound was prepared
  2. 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
Patent number
US08580962B2

Reaction notes

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