2,6-Dibromopyridine → Tert-butyl 4-[3-(6-bromopyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate

HRID 1896034Notes

Reaction equation

HRID 1896034 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CC1N=C(N2CCC(=CC#C)CC2)C([N+]([O-])=O)=CC=1.C[Si](C)(C)C#CC=C1CCNCC1.[Br:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56](Br)[N:55]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Br:53][C:54]1[N:55]=[C:56]([C:3]#[C:4][CH:5]=[C:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 5

HCID 122742,6-DibromopyridineHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 575749824-(3-Trimethylsilylprop-2-ynylidene)piperidineHCID 866273496-Methyl-3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridineHCID 87119414tert-Butyl 4-(3-trimethylsilylprop-2-ynylidene)piperidin-1-carboxyate

Product 1

HCID 87641844Tert-butyl 4-[3-(6-bromopyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylateYield 68%

Procedure

The title compound was prepared from Compound 2a (in place of Compound 274c) following the procedure described for the compound of Example 274, using 2,6-dibromopyridine instead of 1-bromo-3,5-difluorobenzene and adding 1 molar equivalent of tetrabutylammonium fluoride monohydrate to the starting reaction mixture. After the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from 10:0 to 8:2 affording the title product. White solid. Yield: 68%.

Workup

  1. customto the starting reaction mixture
  2. customAfter the work-up, the residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  3. washeluting with PE-EtOAc gradient from 10:0 to 8:2 affording the title product

Sources & evidence

ORD record
ord-9cf7cd3d71874c2db06d7cbee74caaad
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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