Triethylsilane → 6,7-Dimethoxy-4-(5-indolinyloxy)quinoline

HRID 387890ノート

反応式

HRID 387890 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2.C([SiH](CC)CC)C.O.C(=O)(O)O>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19]2

参加物

6

反応物 3

HCID 12052TriethylsilaneHCID 21993411Carbonic acid--water (1/1)HCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

生成物 1

HCID 229364416,7-Dimethoxy-4-(5-indolinyloxy)quinoline収率 79.5%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 6,7-dimethoxy-4-(5-indolyloxy)quinoline (30 mg, 0.0780 mmol, described in WO9717329, p. 52) in trifluoroacetic acid (0.9 ml), triethylsilane (45 ml, 0.2808 mmol, 3.0 eqM) was added while cooling on ice, and the mixture was stirred for 4 hours and 30 minutes at room temperature under a nitrogen atmosphere. After cooling, the reaction solution was diluted with ethyl acetate, neutralized with saturated bicarbonate water, extracted with ethyl acetate, washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/ethanol system) to obtain the title compound (20 mg, 0.0620 mmol, 66.28%) as light yellow crystals.

後処理

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/ethanol system)

出典と根拠

ORDレコード
ord-63624380e9f8407a9cc4ac5aa83ac07b
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

反応ノート

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