Benzene, 2-fluoro-4-methyl-1-nitro- → 2-Methyl-6-{3-[1-(5-methyl-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}pyridine

HRID 1895954Notes

Reaction equation

HRID 1895954 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.F[C:18]1[CH:19]=[C:20]([CH3:27])[CH:21]=[CH:22][C:23]=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:19]=[C:20]([CH3:27])[CH:21]=[CH:22][C:23]=3[N+:24]([O-:26])=[O:25])[CH2:15][CH2:16]2)[N:3]=1

Participants

3

Reactant 2

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 875503972-Methyl-6-{3-[1-(5-methyl-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}pyridineYield 39.9%

Procedure

A well homogenised mixture of the Compound of Example 3 (19 mg, 0.89 mmol) and 3-fluoro-4-nitrotoluene (20.2 mg, 0.13 mmol) was stirred at 120° C. for 0.5 h. The reaction crude was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 2:8 to 3:7) affording the title product (18 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 2:8 to 3:7)

Sources & evidence

ORD record
ord-1588d88639c34764aa77f90b4319d695
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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