2-Bromo-6-methylpyridine → 8-(6-Methyl-3-nitropyridin-2-yl)-3-(pyridin-3-ylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene

HRID 2040847Notes

Reaction equation

HRID 2040847 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH2:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21](C)[N:20]=1>>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11]3([O:16][N:15]=[C:5]([C:4]#[C:3][C:22]4[CH:21]=[N:20][CH:19]=[CH:24][CH:23]=4)[CH2:14]3)[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 792052-Bromo-6-methylpyridineHCID 574938106-Methyl-2-(4-methylene-1-piperidyl)-3-nitropyridine

Product 1

HCID 566460648-(6-Methyl-3-nitropyridin-2-yl)-3-(pyridin-3-ylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene

Procedure

The title compound was prepared following the procedure reported for the compound of Example 3, replacing 3-iodopyridine for 2-bromo-6-methylpyridine. After the usual work-up, the crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 3:7) affording the title product as yellow solid. Yield: 66.7%.

Workup

  1. customThe title compound was prepared
  2. customAfter the usual work-up, the crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 3:7)

Sources & evidence

ORD record
ord-68afeca8aad14cf2a455dac120970913
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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