2-Fluoropyridine → 5-Methyl-6-{4-[3-(6-methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}pyridine-3-carbonitrile

HRID 1895986Notes

Reaction equation

HRID 1895986 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[N:3]=1.F[C:24]1C=CC=C[N:25]=1.[CH3:30]N1C(=O)CCC1>>[CH3:30][C:22]1[CH:21]=[C:20]([C:24]#[N:25])[CH:19]=[N:18][C:17]=1[N:14]1[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 97462-FluoropyridineHCID 13387N-methyl-2-pyrrolidoneHCID 251816392-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridine

Product 1

HCID 875508245-Methyl-6-{4-[3-(6-methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}pyridine-3-carbonitrileYield 81.3%

Procedure

The title compound was prepared following the procedure described for the compound of Example 59, but substituting N,N-dimethylacetamide for NMP and substituting 5-cyano-2-fluoro-3-methylpyridine for 2-fluoropyridine. Purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with EtOAc—Petroleum Ether 2:8. Yellowish solid. Yield: 81.3%.

Workup

  1. customPurification
  2. washeluting with EtOAc—Petroleum Ether 2:8

Sources & evidence

ORD record
ord-65e2e2a520954319b13185b2351e84f2
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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