6-Bromo-2-isopropoxy-4-trifluoromethyl-quinoline → 2-Isopropoxy-4-trifluoromethyl-quinoline-6-carboxylic acid

HRID 2096846Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH:13]([CH3:15])[CH3:14])[CH:6]=[C:5]2[C:16]([F:19])([F:18])[F:17].[C:20]([O:23]CC)(=[O:22])C.O>>[CH:13]([O:12][C:7]1[CH:6]=[C:5]([C:16]([F:19])([F:18])[F:17])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:20]([OH:23])=[O:22])[CH:3]=2)[N:8]=1)([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 222793016-Bromo-2-isopropoxy-4-trifluoromethyl-quinoline

HCID 22728543Water ethylacetate

Product 1

HCID 666970962-Isopropoxy-4-trifluoromethyl-quinoline-6-carboxylic acid

Procedure

The title compound was synthesized by carbonylation of 6-bromo-2-isopropoxy-4-trifluoromethyl-quinoline (CAS [328955-63-1]) in ethyl acetate/water using 50 bar CO, PdCl2 dppf CH2Cl2, 80° C. for 20 h. Light grey solid. MS (m/e, ISP neg. ion)=298.3 [M−H+].

Sources & evidence

ORD record: ord-91c8fe7bb3404ce7b1bf7fd8e0d9bd3e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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