1-(Methylsulphonyl)acetone → 6-Bromo-3-methanesulfonyl-2-methyl-4-(2,4,5-trifluoro-phenyl)-quinoline

HRID 13674

반응식

HRID 13674 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]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19])=O.[CH3:20][S:21]([CH2:24][C:25](=O)[CH3:26])(=[O:23])=[O:22].[Na]>CC(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:25]([CH3:26])[C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[C:9]2[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19]

참가 물질

5

반응물 3

HCID 786951-(Methylsulphonyl)acetoneHCID 5360545SodiumHCID 12001620(2-Amino-5-bromo-phenyl)-(2,4,5-trifluoro-phenyl)-methanone

생성물 1

HCID 120017266-Bromo-3-methanesulfonyl-2-methyl-4-(2,4,5-trifluoro-phenyl)-quinoline수율 20.4%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

(2-Amino-5-bromo-phenyl)-(2,4,5-trifluoro-phenyl)-methanone (compound of example A.4) (1.9 g, 5.7 mmol), methanesulfonylacetone (1.18 g, 8.6 mmol) and sodium tetrachloroaureate(III) dihydrate (0.12 g, 0.28 mmol) were heated at reflux in 2-propanol (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 with a heptane/ethyl acetate gradient from 100:0 to 90:10. One obtained a light yellow solid (0.5 g, 20%). MS: m/z=430 (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 with a heptane/ethyl acetate gradient from 100:0 to 90:10

출처 및 근거

ORD 기록
ord-3a85f4b8f3cc4a6f9babee2cbeed1283
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728142B2

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