Tetramethylammonium fluoride → 2-Chloro-4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-1-methyl-propyl]-phenoxy}-benzonitrile

HRID 2386839Notes

Reaction equation

HRID 2386839 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:38])[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[C:25]([O:30][CH:31]([CH3:33])[CH3:32])[CH:24]=[C:23]4[C:34]([F:37])([F:36])[F:35])=[O:19])=[C:13]([Cl:39])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:40][C:41]([Si](C)(C)C)([F:43])[F:42].[F-].C[N+](C)(C)C>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:38])[C:18]([OH:19])([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[C:25]([O:30][CH:31]([CH3:33])[CH3:32])[CH:24]=[C:23]4[C:34]([F:35])([F:37])[F:36])[C:41]([F:43])([F:42])[F:40])=[C:13]([Cl:39])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 67803Tetramethylammonium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 66697136HCID 66697136, compound

Product 1

HCID 866458812-Chloro-4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-1-methyl-propyl]-phenoxy}-benzonitrile

Procedure

In analogy to Example 1, step 3, 2-chloro-4-{3-chloro-4-[2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-1-methyl-2-oxo-ethyl]-phenoxy}-benzonitrile was reacted with (trifluoromethyl)trimethylsilane and tetramethylammonium fluoride to give the title compound as an off-white gum. MS (m/e, ISP neg. ion)=641.1 [M−H+].

Sources & evidence

ORD record
ord-422a3b455a454372ac304e10bb8fb158
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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