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

HRID 1895953

Reaction equation

HRID 1895953 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][NH:14][CH2:13][CH2:12]2)[N:3]=1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26]>>[CH3:24][C:22]1[N:23]=[C:18]([N:14]2[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=3)[CH2:16][CH2:15]2)[C:19]([N+:25]([O-:27])=[O:26])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 251475086-Methyl-2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridineYield 54.8%

Procedure

A well homogenised mixture of the Compound of Example 3 (23 mg, 0.11 mmol) and 6-chloro-5-nitro-2-picoline (26.2 mg, 0.15 mmol) was stirred at 120° C. for 0.5 h. The reaction crude was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 3:7 to 4:6) affording the title product (21 mg).

Workup

  1. stirringwas stirred at 120° C. for 0.5 h
  2. customThe reaction crude
  3. customwas purified by flash chromatography (EtOAc—Petroleum Ether gradient from 3:7 to 4:6)

Sources & evidence

ORD record
ord-eecdb9d2fa4f4167b12bd36a3a080539
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Linked notes

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