3-Fluoro-4-nitroanisole → 2-{3-[1-(5-Methoxy-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}-6-methylpyridine

HRID 1895955Notes

Reaction equation

HRID 1895955 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:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]>>[CH3:25][O:24][C:22]1[CH:21]=[CH:20][C:19]([N+:26]([O-:28])=[O:27])=[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)[CH:23]=1

Participants

3

Reactant 2

HCID 5656543-Fluoro-4-nitroanisoleHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 251836722-{3-[1-(5-Methoxy-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl}-6-methylpyridineYield 48.2%

Procedure

A well homogenised mixture of the Compound of Example 3 (20 mg, 0.93 mmol) and 2-fluoro-4-methoxynitrobenzene (21.3 mg, 0.12 mmol) was stirred at 120° C. for 0.5 h. The reaction crude was purified by flash chromatography (EtOAc—Petroleum Ether 1:1) 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 1:1)

Sources & evidence

ORD record
ord-39a9851e51bb435f8577bb27293eea9e
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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