2-Fluoropyridine → 2-{4-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidin-1-yl}-6-methylnicotinonitrile

HRID 1896030Notes

Reaction equation

HRID 1896030 reaction equation
CC1C=CC=C(C#CC=C2CCN(C3C=CC=CN=3)CC2)N=1.FC1C=CC=CN=1.[F:30][C:31]1[CH:32]=[C:33]([C:38]#[C:39][CH:40]=[C:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH:34]=[C:35]([F:37])[CH:36]=1.Cl[C:48]1[N:55]=[C:54]([CH3:56])[CH:53]=[CH:52][C:49]=1[C:50]#[N:51].C(=O)([O-])[O-].[K+].[K+]>>[F:30][C:31]1[CH:32]=[C:33]([C:38]#[C:39][CH:40]=[C:41]2[CH2:42][CH2:43][N:44]([C:48]3[N:55]=[C:54]([CH3:56])[CH:53]=[CH:52][C:49]=3[C:50]#[N:51])[CH2:45][CH2:46]2)[CH:34]=[C:35]([F:37])[CH:36]=1

Participants

6

Reactant 5

HCID 97462-FluoropyridineHCID 11430Potassium CarbonateHCID 5204002-Chloro-6-methylpyridine-3-carbonitrileHCID 251816392-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridineHCID 866273424-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidine

Product 1

HCID 866273502-{4-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidin-1-yl}-6-methylnicotinonitrileYield 61%

Procedure

The title compound was synthesized following the procedure reported for the compound of Example 59 replacing the compound of Example 3, 2-fluoropyridine and TEA respectively with Compound 228b, 2-chloro-6-methylnicotinonitrile and potassium carbonate. Purification by automated flash chromatography (Horizon™-Biotage) eluting with PE-EtOAc 95:5. Yellow solid. Yield: 61%

Workup

  1. customPurification by automated flash chromatography (Horizon™-Biotage)
  2. washeluting with PE-EtOAc 95:5

Sources & evidence

ORD record
ord-fb4cd8366517469a959528eaf506384b
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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