1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 6-Methyl-[4-{3-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]prop-2-ynylidene}piperidin-1-yl]-3-nitropyridine

HRID 1896047Notes

Reaction equation

HRID 1896047 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[CH:16])[CH2:10][CH2:9]2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.C[Si](C)(C)C#CC=C1CCNCC1.Br[C:34]1[CH:35]=[C:36]([C:40]2[O:44][N:43]=[C:42]([CH3:45])[N:41]=2)[CH:37]=[CH:38][CH:39]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[C:16][C:38]3[CH:39]=[CH:34][CH:35]=[C:36]([C:40]4[O:44][N:43]=[C:42]([CH3:45])[N:41]=4)[CH:37]=3)[CH2:10][CH2:9]2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 197031245-(3-Bromophenyl)-3-methyl-1,2,4-oxadiazoleHCID 575749824-(3-Trimethylsilylprop-2-ynylidene)piperidineHCID 866273496-Methyl-3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Product 1

HCID 866273596-Methyl-[4-{3-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]prop-2-ynylidene}piperidin-1-yl]-3-nitropyridineYield 61%

Procedure

The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 using 5-(3-bromophenyl)-3-methyl-1,2,4-oxadiazole 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 (SP1™-Biotage) eluting with PE-EtOAc gradient from 9:1 to 7:3 affording the title product. Yellow oil. Yield: 61%.

Workup

  1. customto the starting reaction mixture
  2. customAfter the work-up, the residue was purified by automated flash liquid chromatography (SP1™-Biotage)
  3. washeluting with PE-EtOAc gradient from 9:1 to 7:3 affording the title product

Sources & evidence

ORD record
ord-4f982640478e477c946b488c7fdcb6a7
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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