2-Chloro-6-methyl-3-nitropyridine → 2-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-yl]but-3-yn-2-ol

HRID 1896044Notes

Reaction equation

HRID 1896044 reaction equation
CC1N=C(C#CC(C2CCNCC2)O)C=CC=1.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]([OH:28])([C:26]#[CH:27])[CH3:25])[CH2:20][CH2:19]1.Cl[C:30]1[C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=[C:32]([CH3:39])[N:31]=1>>[CH3:39][C:32]1[N:31]=[C:30]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:28])([C:26]#[CH:27])[CH3:25])[CH2:20][CH2:19]2)[C:35]([N+:36]([O-:38])=[O:37])=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 689774953-(6-Methyl-pyridin-2-yl)-1-piperidin-4-yl-prop-2-yn-1-olHCID 866273582-(Piperidin-4-yl)but-3-yn-2-ol

Product 1

HCID 866273572-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-yl]but-3-yn-2-olYield 93%

Procedure

The title compound was prepared as described for the compound of Example 237 but starting from Compound 312b instead of Compound 237a and 2-chloro-6-methyl-3-nitropyridine instead of 2-bromo-3-nitropyridine. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc from PE:EtOAc 9:1 affording the title products as yellow oil. Yield: 93%.

Workup

  1. customAfter the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  2. washeluting with PE-EtOAc from PE

Sources & evidence

ORD record
ord-a12fff2d69c64735afc46742a3efac5a
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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