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1-(Methylsulphonyl)acetone → 6-Bromo-3-methanesulfonyl-2-methyl-4-(4-trifluoromethyl-phenyl)-quinoline

HRID 13673
Notes
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Reaction equation

HRID 13673 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=O.[CH3:21][S:22]([CH2:25][C:26](=O)[CH3:27])(=[O:24])=[O:23].[Na]>C(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:26]([CH3:27])[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[C:9]2[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 786951-(Methylsulphonyl)acetoneHCID 5360545SodiumHCID 12001533(2-Amino-5-bromo-phenyl)-(4-trifluoromethyl-phenyl)-methanone

Product 1

HCID 120017256-Bromo-3-methanesulfonyl-2-methyl-4-(4-trifluoromethyl-phenyl)-quinolineYield 29.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2-Amino-5-bromo-phenyl)-(4-trifluoromethyl-phenyl)-methanone (compound of example A.3) (4 g, 11.6 mmol), methanesulfonylacetone (2.37 g, 17.4 mmol) and sodium tetrachloroaureate(III) dihydrate (0.23 g, 0.58 mmol) were heated at reflux in ethanol (50 ml) for 4 days. The resulting mixture was evaporated to dryness and the residue extracted with dichloromethane (2×), NaOH (2×) and NaCl (1×). The crude product was purified by chromatography on silica gel in heptane/ethyl acetate 70:30. One obtained a light yellow solid (1.5 g, 29%). MS: m/z=444 (M).

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. extractionthe residue extracted with dichloromethane (2×), NaOH (2×) and NaCl (1×)
  3. customThe crude product was purified by chromatography on silica gel in heptane/ethyl acetate 70:30

Sources & evidence

ORD record
ord-7da5d5e5e52a4a668d4398aaa7b5faaa
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728142B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes