2-Bromo-6-methylpyridine → 2-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-yl]-4-(6-methylpyridin-2-yl)but-3-yn-2-ol

HRID 1896045Notes

Reaction equation

HRID 1896045 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:18])([C:16]#[CH:17])[CH3:15])[CH2:10][CH2:9]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=1>>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:18])([C:16]#[C:17][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=3)[CH3:15])[CH2:10][CH2:9]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 792052-Bromo-6-methylpyridineHCID 866273572-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-yl]but-3-yn-2-ol

Product 1

HCID 251817812-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-yl]-4-(6-methylpyridin-2-yl)but-3-yn-2-olYield 41%

Procedure

According to the Method B detailed for Examples 218-226 starting from Compound 312c and using 2-bromo-6-methylpyridine the title compound was prepared. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 1:1 affording the title product as a yellow oil. Yield: 41%.

Sources & evidence

ORD record
ord-bdbe8eed22e54141af17986dd19c010a
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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