2-Isopropoxy-4-trifluoromethyl-quinoline-6-carboxylic acid → 2-Chloro-4-{3-chloro-4-[2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-2-oxo-ethyl]-phenoxy}-benzonitrile

HRID 2386837Notes

Reaction equation

HRID 2386837 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:19](O)=[O:20])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2].CN1C2C=CC(C(Cl)=O)=CC=2OC1=O.Br[CH2:37][C:38]1[CH:53]=[CH:52][C:41]([O:42][C:43]2[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[C:45]([Cl:51])[CH:44]=2)=[CH:40][C:39]=1[Cl:54]>[Zn]>[Cl:51][C:45]1[CH:44]=[C:43]([O:42][C:41]2[CH:52]=[CH:53][C:38]([CH2:37][C:19]([C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[N:6]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:14]=[C:13]4[C:15]([F:16])([F:17])[F:18])=[O:20])=[C:39]([Cl:54])[CH:40]=2)[CH:50]=[CH:49][C:46]=1[C:47]#[N:48]

Participants

5

Reactant 3

HCID 666970962-Isopropoxy-4-trifluoromethyl-quinoline-6-carboxylic acidHCID 666971204-(4-Bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrileHCID 866458793-Methyl-2-oxo-2,3-dihydro-benzooxazole-6-carbonyl chloride

Product 1

HCID 666971182-Chloro-4-{3-chloro-4-[2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-2-oxo-ethyl]-phenoxy}-benzonitrile

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In analogy to Example 49, step 1, 2-isopropoxy-4-trifluoromethyl-quinoline-6-carboxylic acid was converted to the acid chloride and subsequently reacted with 4-(4-bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrile in the presence of zinc and tetrakis(triphenyl-phosphine)palladium(0) to give the title compound as a yellow oil. MS (m/e, ISP neg. ion)=557.0 [M−H+].

Sources & evidence

ORD record
ord-5d535dea7b784f30b2c47d8405044edb
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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