Iodobenzene → 3-Nitro-2-[4-(3-phenylprop-2-ynylidene)piperidin-1-yl]pyridine

HRID 1895957Notes

Reaction equation

HRID 1895957 reaction equation
C[Si](C)(C)C#CCP(=O)(OCC)OCC.[N+:16]([C:19]1[C:20]([N:25]2[CH2:30][CH2:29][C:28](=[CH:31][C:32]#[CH:33])[CH2:27][CH2:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[N+:16]([C:19]1[C:20]([N:25]2[CH2:30][CH2:29][C:28](=[CH:31][C:32]#[C:33][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:27][CH2:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 11575IodobenzeneHCID 10933869Diethyl (3-trimethylsilylprop-2-ynyl)phosphonateHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Product 1

HCID 251836733-Nitro-2-[4-(3-phenylprop-2-ynylidene)piperidin-1-yl]pyridine

Procedure

The title compound was obtained as described for the Compound of Example 1, reacting Compound 1c with iodobenzene instead of 2-bromo-6-methylpyridine. Purification by flash chromatography with Petroleum Ether-EtOAc 65:35 afforded the title product.

Workup

  1. customPurification by flash chromatography with Petroleum Ether-EtOAc 65:35

Sources & evidence

ORD record
ord-aaf673349cb14229ae44ae73c64bf2df
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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