N-(3-Bromophenyl)acetamide → 3-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenylacetamide

HRID 1896040Notes

Reaction equation

HRID 1896040 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:22]#[C:23][CH:24]=[C:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CC(NC1C=CC=C(Br)C=1)=[O:35].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:27]3[CH:26]=[C:25]([CH2:30][C:29]([NH2:28])=[O:35])[CH:24]=[CH:23][CH:22]=3)[CH2:10][CH2:9]2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 12123N-(3-Bromophenyl)acetamideHCID 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 866273533-{3-[1-(6-Methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}phenylacetamideYield 54%

Procedure

The title Compound was prepared from Compound 274c following the procedure described for the compound of Example 274 using 3-bromoacetanilide 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 7:3 to 4:6 affording the title product. Orange oil. Yield: 54%.

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 7:3 to 4:6 affording the title product

Sources & evidence

ORD record
ord-a6bae25e56dc48dda12a8f816d8348c1
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…