2-Chloro-6-methylpyridine-3-carbonitrile → HCID 87550782, compound

HRID 1896033Notes

Reaction equation

HRID 1896033 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](C3C=NC=C(C(F)(F)F)C=3)[CH2:13][CH2:12]2)N=1.Br[C:28]1C=NC=C(C(F)(F)F)C=1.Cl[C:39]1[N:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:40]=1[C:41]#[N:42].CC1C=CC=C(C#CC=C2CCNCC2)N=1>>[CH3:47][C:45]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[C:39]([N:14]2[CH2:13][CH2:12][C:11](=[C:10]([CH3:28])[C:9]#[C:8][C:4]3[CH:1]=[CH:2][CH:7]=[CH:6][CH:5]=3)[CH2:16][CH2:15]2)[N:46]=1

Participants

5

Reactant 4

HCID 5204002-Chloro-6-methylpyridine-3-carbonitrileHCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 25181651HCID 25181651, compoundHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87550782HCID 87550782, compoundYield 35%

Procedure

The title compound was synthesized following the procedure described for the Compound of Example 262 replacing 3-bromo-5-(trifluoromethyl)pyridine with 2-chloro-6-methylnicotinonitrile and the compound of Example 3 with Compound 253d. Purification by automated flash chromatography (Horizon™-Biotage) PE-EtOAc 9:1 afforded a colorless oil. Yield: 35%.

Workup

  1. customPurification by automated flash chromatography (Horizon™-Biotage) PE-EtOAc 9:1
  2. customafforded a colorless oil

Sources & evidence

ORD record
ord-f8e1504325b24e858722a281b7add993
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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