2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine → 2-Bromo-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

HRID 1896035Notes

Reaction equation

HRID 1896035 reaction equation
CC1C=CC=C(C#CC=C2CCNCC2)N=1.[Br:17][C:18]1[N:23]=[C:22]([C:24]#[C:25][CH:26]=[C:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)[CH:21]=[CH:20][CH:19]=1>>[Br:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([C:24]#[C:25][CH:26]=[C:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[N:23]=1

Participants

3

Reactant 2

HCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridineHCID 87641844Tert-butyl 4-[3-(6-bromopyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate

Product 1

HCID 876422122-Bromo-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Procedure

The title product was prepared following the method described for the Compound of Example 3 but using as starting material Compound 305a instead of the Compound of Example 2 and stirring at ambient temperature for 3 days. The reaction mixture was evaporated to dryness in vacuo, taking up the residue several times with chloroform to remove excess trifluoroacetic acid.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customto remove excess trifluoroacetic acid

Sources & evidence

ORD record
ord-213125f6597a4d6fa6d15b244e585472
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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