Dabco → 6-{3-Chloro-4-[2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-2-methyl-nicotinonitrile

HRID 1096050Notes

Reaction equation

HRID 1096050 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:25])[C:10]([C:16]1[CH:17]=[C:18]([CH3:24])[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[C:26]([C:28]1[CH:29]=[CH:30][C:31](F)=[N:32][C:33]=1[CH3:34])#[N:27].N12CCN(CC1)CC2>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:9]([CH3:25])[C:10]([C:16]1[CH:17]=[C:18]([CH3:24])[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1)([OH:15])[C:11]([F:13])([F:14])[F:12])[O:8][C:31]1[CH:30]=[CH:29][C:28]([C:26]#[N:27])=[C:33]([CH3:34])[N:32]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 404186196-Fluoro-2-methylpyridine-3-carbonitrileHCID 666993015-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1H-pyridin-2-one

Product 1

HCID 666994096-{3-Chloro-4-[2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-2-methyl-nicotinonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In analogy to Example 163, 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1H-pyridin-2-one (Example 203, step 5) was reacted with 5-cyano-2-fluoro-6-picoline in the presence of triethylamine and 1,4-diazabicyclo[2.2.2]octane to give the title compound as a colorless solid. MS (m/e)=492.1 [M+H+].

Sources & evidence

ORD record
ord-e6755697d1204d22a66cddea13fa8fcd
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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