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

HRID 13673노트

반응식

HRID 13673 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-7da5d5e5e52a4a668d4398aaa7b5faaa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728142B2

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