2-Chloro-4-fluoropyridine → Tert-butyl 4-[3-(4-fluoropyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate

HRID 1896027Notes

Reaction equation

HRID 1896027 reaction equation
FC1C=C(C#CC=C2CCN(C3C([N+]([O-])=O)=CC=CN=3)CC2)C=C(F)C=1OC.[CH:29](=[C:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)[C:30]#[CH:31].Cl[C:46]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][N:47]=1>>[F:52][C:50]1[CH:49]=[CH:48][N:47]=[C:46]([C:31]#[C:30][CH:29]=[C:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)[CH:51]=1

Participants

4

Reactant 3

HCID 27827922-Chloro-4-fluoropyridineHCID 866273392-(4-(3-(3,5-Difluoro-4-methoxyphenyl)prop-2-yn-1-ylidene)piperidin-1-yl)-3-nitropyridineHCID 86661548tert-Butyl 4-(prop-2-yn-1-ylidene)piperidine-1-carboxylate

Product 1

HCID 91261370Tert-butyl 4-[3-(4-fluoropyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylateYield 38.5%

Procedure

The title compound was prepared following the procedure described for the Compound of Example 199, but using Compound 2b instead of Compound 1c and 2-chloro-4-fluoropyridine instead of 4-bromo-2,6-difluoroanisole. After the usual work-up procedure, purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from 95:5 to 60:40. Yield: 38.5%.

Workup

  1. customAfter the usual work-up procedure, purification
  2. washeluting with PE-EtOAc gradient from 95:5 to 60:40

Sources & evidence

ORD record
ord-1b7572d6b1e64c24aef166b5893311d3
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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