3-Bromophenetole → 2-{4-[3-(3-Ethoxyphenyl)prop-2-ynylidene]piperidin-1-yl}-6-methyl-3-nitropyridine

HRID 1896038Notes

Reaction equation

HRID 1896038 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.[CH2:33]([O:35][C:36]1[CH:37]=[C:38](Br)[CH:39]=[CH:40][CH:41]=1)[CH3:34].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:33]([O:35][C:36]1[CH:41]=[C:40]([C:16]#[C:15][CH:14]=[C:11]2[CH2:12][CH2:13][N:8]([C:6]3[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:9][CH2:10]2)[CH:39]=[CH:38][CH:37]=1)[CH3:34]

Participants

5

Reactant 4

HCID 758673-BromophenetoleHCID 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 866273522-{4-[3-(3-Ethoxyphenyl)prop-2-ynylidene]piperidin-1-yl}-6-methyl-3-nitropyridineYield 46%

Procedure

The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 but using 3-ethoxybromobenzene 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 PE:EtAc 1:0 to 8:2 affording the title product. Yellow solid. Yield: 46%.

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 PE

Sources & evidence

ORD record
ord-122d1bac94834940b0d2fe42f525318a
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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