Triethylamine → 7-(2-benzenesulfonylvinyl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

HRID 244812

반응식

HRID 244812 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[CH:26]([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])=[CH2:27].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[C:31]1([S:28]([CH:26]=[CH:27][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=4[CH:8]=[N:9][C:10]=3[CH:11]=2)(=[O:30])=[O:29])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 79664Phenyl vinyl sulfoneHCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 690814007-(2-benzenesulfonylvinyl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline수율 49.4%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (1.00 g, 2.46 mmol), phenyl vinyl sulfone (0.852 g, 5.06 mmol), palladium(II) acetate (12 mg, 0.05 mmol), and tris(2-tolyl)phosphine (32 mg, 0.10 mmol) were added to a pressure tube. Triethylamine (1.37 mL, 9.84 mmol) and acetonitrile (5 mL) were added. The tube was flushed with nitrogen, sealed with a TEFLON plug and heated at 100° C. for 96 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was initially purified by flash column chromatography (silica gel, eluting with a gradient of 50%-100% ethyl acetate in hexanes, followed by a gradient of 2%-6% methanol in ethyl acetate). Recrystallization of the resulting solid from acetonitrile provided 0.600 g 7-(2-benzenesulfonylvinyl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline as a yellow crystalline solid.

후처리

  1. customThe tube was flushed with nitrogen
  2. customsealed with a TEFLON plug
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was initially purified by flash column chromatography (silica gel
  6. washeluting with a gradient of 50%-100% ethyl acetate in hexanes
  7. customRecrystallization of the resulting solid from acetonitrile

출처 및 근거

ORD 기록
ord-094daf7fc0244d8385c9bad4fa4b3936
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658666B2

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