2-Bromo-5-nitropyridine → 2-{4-[3-(6-Methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}-5-nitropyridine

HRID 1895981Notes

Reaction equation

HRID 1895981 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[N:3]=1.BrC1C=CC([N+:30]([O-:32])=[O:31])=CN=1>CN(C)C(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:30]([O-:32])=[O:31])=[CH:19][N:18]=3)[CH2:15][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 782402-Bromo-5-nitropyridineHCID 251816392-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridine

Product 1

HCID 875506712-{4-[3-(6-Methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was prepared following the procedure described for the compound of Example 59, but substituting NMP with N,N-dimethylacetamide and substituting 2-fluoropyridine with 2-bromo-5-nitropyridine. Purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with CHCl3-1.4 N MeOH NH3 100:0.5.

Workup

  1. customPurification
  2. washeluting with CHCl3-1.4 N MeOH NH3 100:0.5

Sources & evidence

ORD record
ord-9b8fa889d10b461582da524692ca48a1
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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