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

HRID 2040845Notes

Reaction equation

HRID 2040845 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[CH3:9][C:10]1[N:15]=[C:14]([N:16]2[CH2:21][CH2:20][C:19](=[CH2:22])[CH2:18][CH2:17]2)[C:13]([N+:23]([O-:25])=[O:24])=[CH:12][CH:11]=1>>[CH3:9][C:10]1[N:15]=[C:14]([N:16]2[CH2:21][CH2:20][C:19]3([O:24][N:23]=[C:13]([C:12]#[C:8][C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][N:3]=4)[CH2:22]3)[CH2:18][CH2:17]2)[C:13]([N+:23]([O-:25])=[O:24])=[CH:12][CH:11]=1

Participants

3

Reactant 2

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

Product 1

HCID 566456788-(6-Methyl-3-nitropyridin-2-yl)-3-(pyridin-2-ylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-eneYield 49.6%

Procedure

The title product was prepared replacing 2-iodopyridine for 2-bromo-6-methylpyridine following the procedure reported above for the compound of Example 3. Purification of the residue by automated flash liquid chromatography (Horizon®TM-Biotage) (Petroleum Ether-EtOAc gradient from 9:1 to 4:6). Yield: 49.6%.

Workup

  1. customPurification of the residue by automated flash liquid chromatography (Horizon®TM-Biotage) (Petroleum Ether-EtOAc gradient from 9:1 to 4:6)

Sources & evidence

ORD record
ord-06f3761db6d54a1db5b477fdd8dc0f85
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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