Ethanone, 1-(3-iodophenyl)- → 1-(3-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenyl)ethanone

HRID 1896039Notes

Reaction equation

HRID 1896039 reaction equation
F[C:2]1[CH:3]=[C:4]([C:11]#[C:12][CH:13]=[C:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH:5]=[C:6](F)[C:7]=1OC.[N+]([C:32]1C(N2CCC(=CC#C)CC2)=NC=CC=1)([O-])=O.IC1C=[C:50]([C:54](=[O:56])C)C=CC=1.BrC1C=C(F)C(OC)=C(F)C=1>>[CH3:32][C:22]1[N:21]=[C:20]([N:17]2[CH2:16][CH2:15][C:14](=[CH:13][C:12]#[C:11][C:4]3[CH:5]=[C:6]([C:54](=[O:56])[CH3:50])[CH:7]=[CH:2][CH:3]=3)[CH2:19][CH2:18]2)[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 84449Ethanone, 1-(3-iodophenyl)-HCID 27732874-Bromo-2,6-difluoroanisoleHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridineHCID 866273392-(4-(3-(3,5-Difluoro-4-methoxyphenyl)prop-2-yn-1-ylidene)piperidin-1-yl)-3-nitropyridine

Product 1

HCID 875501061-(3-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenyl)ethanoneYield 84.3%

Procedure

The title compound was prepared in the same way as the Compound of Example 199 but substituting Compound 274c for Compound 1c and 1-(3-iodophenyl)ethanone for 4-bromo-2,6-difluoranisole. After the work-up, the residue was purified by automated flash liquid chromatography (SP1™-Biotage) eluting with PE-EtOAc gradient from 9:1 to 8:2 affording the title product. Yellow oil. Yield: 84.3%.

Workup

  1. customAfter the work-up, the residue was purified by automated flash liquid chromatography (SP1™-Biotage)
  2. washeluting with PE-EtOAc gradient from 9:1 to 8:2 affording the title product

Sources & evidence

ORD record
ord-82fa4e8a1404414fb3fa4a21ce3d7f3a
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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