2-Chloro-6-methyl-3-nitropyridine → 6-Methyl-2-[4-[3-(6-bromo-2-pyridyl)prop-2-ynylidene]piperidin-1-yl]nicotinonitrile

HRID 1896037Notes

Reaction equation

HRID 1896037 reaction equation
C[C:2]1[N:7]=[C:6]([C:8]#CC(C2CCNCC2)O)[CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][CH:27]=[C:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[N:20]=1.Cl[C:35]1C([N+]([O-])=O)=CC=C(C)[N:36]=1>>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([C:35]#[N:36])=[C:2]([N:31]2[CH2:32][CH2:33][C:28](=[CH:27][C:26]#[C:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([Br:18])[N:20]=3)[CH2:29][CH2:30]2)[N:7]=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 876422122-Bromo-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 876416386-Methyl-2-[4-[3-(6-bromo-2-pyridyl)prop-2-ynylidene]piperidin-1-yl]nicotinonitrileYield 95%

Procedure

The title compound was prepared as described for the compound of Example 237 but starting from Compound 305b instead of compound 237a and 2-chloro-6-methyl-3-nitropyridine instead of 2-bromo-3-nitropyridine. An additional equivalent of TEA was used. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from PE:EtAc 95:5 to 6:4 affording the title product. Yellow oil. Yield: 95%.

Workup

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

Sources & evidence

ORD record
ord-6644481c14944a898d4c77ea8239f089
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…