1-Bromo-2-nitrobenzene → 2-Methyl-6-{3-[1-(2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}pyridine

HRID 1895952Notes

Reaction equation

HRID 1895952 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.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-:26])=[O:25])[CH2:15][CH2:16]2)[N:3]=1

Participants

3

Reactant 2

HCID 113411-Bromo-2-nitrobenzeneHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 251836702-Methyl-6-{3-[1-(2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}pyridineYield 27.7%

Procedure

A well homogenised mixture of the Compound of Example 3 (20 mg, 0.09 mmol) and 1-bromo-2-nitrobenzene (22.8 mg, 0.11 mmol) was stirred at 90° C. for 0.5 h, then at 110° C. for 1 h. The reaction crude was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 3:7 to 4:6) affording the title product (8.3 mg).

Workup

  1. stirringwas stirred at 90° 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-ae27f68ae5a141c9a44320aaee8b519f
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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