1-(3-Bromophenyl)propan-2-one → (1-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenyl)acetone

HRID 1896041Notes

Reaction equation

HRID 1896041 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]([CH2:40][C:41](=[O:43])[CH3:42])[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:36]3([CH2:40][C:41](=[O:43])[CH3:42])[CH:35]=[CH:34][CH:39]=[CH:38][CH2:37]3)[CH2:10][CH2:9]2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 27340931-(3-Bromophenyl)propan-2-oneHCID 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)pyridine

Product 1

HCID 86627354(1-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenyl)acetoneYield 41%

Procedure

The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 using 3-bromophenylacetone 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. Orange oil. Yield: 41%.

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-bf2f12608306407f89140b2dc03a3966
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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