Aluminium lithium hydride → 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 509845ノート

反応式

HRID 509845 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=O)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1>C1COCC1>[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][CH2:21][N:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 578763372-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone

生成物 1

HCID 578762952,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole収率 22.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

LAH (0.022 g, 0.58 mmol) was charged in dry THF (3 mL) and cooled to 0 deg C., 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone (0.05 g, 0.147 mmol) was added to it portion wise. The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to 0 deg C. and quenched with sat. Na2SO4. The solid formed was filtered through celite, washed with THF, dried over Na2SO4 and concentrated under reduced pressure to obtain 11 mg of 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

後処理

  1. temperaturecooled to 0 deg C
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. temperatureThe reaction mixture was cooled to 0 deg C
  4. customand quenched with sat. Na2SO4
  5. customThe solid formed
  6. filtrationwas filtered through celite
  7. washwashed with THF
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5dc8f0a8c9ba48a6a88d8011fbc525e9
出典データセット
uspto-grants-2015_08
特許番号
US09096591B2

反応ノート

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