1-Fluoro-3-iodobenzene → 2-{4-[3-(3-Fluorophenyl)prop-2-ynylidene]piperidin-1-yl}-6-methylnicotinonitrile

HRID 1896031Notes

Reaction equation

HRID 1896031 reaction equation
C[Si](C)(C)C#CC=C1CC[NH:9][CH2:8]C1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.[CH3:22][C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][C:32](=[CH:35][C:36]#[CH:37])[CH2:31][CH2:30]2)[C:26]([N+]([O-])=O)=[CH:25][CH:24]=1>>[F:14][C:15]1[CH:16]=[C:17]([C:37]#[C:36][CH:35]=[C:32]2[CH2:33][CH2:34][N:29]([C:27]3[N:28]=[C:23]([CH3:22])[CH:24]=[CH:25][C:26]=3[C:8]#[N:9])[CH2:30][CH2:31]2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 707251-Fluoro-3-iodobenzeneHCID 575749824-(3-Trimethylsilylprop-2-ynylidene)piperidineHCID 866273496-Methyl-3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Product 1

HCID 875498222-{4-[3-(3-Fluorophenyl)prop-2-ynylidene]piperidin-1-yl}-6-methylnicotinonitrile

Procedure

The title compound was prepared in the same way as the Compound of Example 274 but replacing 1-bromo-3,5-difluorobenzene with 1-fluoro-3-iodobenzene and Compound 274c with Compound 284a. The residue coming from the work-up procedure was purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient affording the title compound as a colourless oil. Yield: 20.4%

Workup

  1. customwas purified by preparative RP LC-MS chromatography
  2. washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient

Sources & evidence

ORD record
ord-711e128cbe7a4a95bd615e5f09e3d555
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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