2-Chloro-6-methyl-3-nitropyridine → 2-{4-[3-(3,5-Difluorophenyl)prop-2-yn-yl]piperidin-1-yl}-6-methyl-3-nitropyridine

HRID 1896000Notes

Reaction equation

HRID 1896000 reaction equation
CC1N=C(C#CC(C2CCNCC2)O)C=CC=1.[F:18][C:19]1[CH:20]=[C:21]([C:26]#[C:27][CH2:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:22]=[C:23]([F:25])[CH:24]=1.Cl[C:36]1[C:41]([N+:42]([O-:44])=[O:43])=[CH:40][CH:39]=[C:38]([CH3:45])[N:37]=1>>[F:18][C:19]1[CH:20]=[C:21]([C:26]#[C:27][CH2:28][CH:29]2[CH2:30][CH2:31][N:32]([C:36]3[C:41]([N+:42]([O-:44])=[O:43])=[CH:40][CH:39]=[C:38]([CH3:45])[N:37]=3)[CH2:33][CH2:34]2)[CH:22]=[C:23]([F:25])[CH:24]=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 689794914-[3-(3,5-Difluorophenyl)prop-2-ynyl]piperidine

Product 1

HCID 251817892-{4-[3-(3,5-Difluorophenyl)prop-2-yn-yl]piperidin-1-yl}-6-methyl-3-nitropyridine

Procedure

The title compound was prepared following the procedure described for the compound of Example 237, but using Compound 248a instead of Compound 237a and 2-chloro-3-nitro-6-picoline instead of 2-bromo-3-nitropyridine. The crude was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 9:1, affording the title product as a yellow oil.

Workup

  1. customThe title compound was prepared
  2. customThe crude was purified by automated flash liquid chromatography (Horizon™-Biotage)
  3. washeluting with Petroleum Ether-EtOAc 9:1

Sources & evidence

ORD record
ord-c52dda0fc7454939a7637727c66f0284
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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