2-Chloro-6-methyl-3-nitropyridine → HCID 86627355, compound

HRID 1896042Notes

Reaction equation

HRID 1896042 reaction equation
CC1N=C(C#CC(C2CCNCC2)O)C=CC=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26]/[CH:27]=[C:28]2\[CH2:29][NH:30][CH2:31][CH2:32][CH2:33]\2)[N:20]=1.Cl[C:35]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=[C:37]([CH3:44])[N:36]=1>>[CH3:44][C:37]1[N:36]=[C:35]([N:30]2[CH2:31][CH2:32][CH2:33]/[C:28](=[CH:27]\[C:26]#[C:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([CH3:18])[N:20]=3)/[CH2:29]2)[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=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 86627356HCID 86627356, compound

Product 1

HCID 86627355HCID 86627355, compound

Procedure

The title compound was prepared as described for the compound of Example 237 but starting from Compound 310c or 311c instead of compound 237a and using 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 (SP1™-Biotage) eluting with PE-EtOAc gradient from PE-EtOAc 7:3 to 6:4 affording the title products. Example 310:18%. Example 310: 11%

Workup

  1. customAfter the work-up, the residue was purified by automated flash liquid chromatography (SP1™-Biotage)
  2. washeluting with PE-EtOAc gradient from PE-EtOAc 7:3 to 6:4 affording the title products

Sources & evidence

ORD record
ord-a4d76025baad4d81b38041b82370c62d
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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