Triethylamine → 6-bromo-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinolin-2(1H)-one

HRID 623961Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=O)[C:10]([F:13])([F:12])[F:11].[Cl:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](Cl)=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:22](=[O:23])[C:21]([O:20][C:19]1[CH:25]=[CH:26][C:16]([Cl:15])=[CH:17][CH:18]=1)=[C:9]2[C:10]([F:13])([F:12])[F:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(2-amino-5-bromophenyl)-2,2,2-trifluoroethanone (2.76 g, 10.3 mmol, Intermediate 7, step b) in dichloromethane (20 mL) was added commercially available 2-(4-chlorophenoxy)acetyl chloride (2.11 g, 10.3 mmol). The resulting white solution was cooled with an ice bath to 0° C. and treated with triethylamine (4.29 mL, 30.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 12 hours and at 60° C. for 2 hours. The mixture was diluted with dichloromethane at room temperature and washed with water. The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, 25% EtOAc-Heptane), affording the title compound.

Workup

washwashed with water
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash column chromatography (silica gel, 25% EtOAc-Heptane)

Sources & evidence

ORD record: ord-2f6339c8b1f541a1beaa4dda377f1004
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303015B2

Reaction notes

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