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Acrylonitrile → 3-(8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)propanenitrile

HRID 1773244
ノート
印刷プレビュー

反応式

HRID 1773244 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:6]3[CH2:20][CH2:21][NH:22][CH2:23][C:5]=3[C:4]=2[CH:3]=1.[C:24](#[N:27])[CH:25]=[CH2:26].N([O-])=O.[NH4+].C([O-])(O)=O.[Na+]>O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:6]3[CH2:20][CH2:21][N:22]([CH2:26][CH2:25][C:24]#[N:27])[CH2:23][C:5]=3[C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7855AcrylonitrileHCID 26004Ammonium nitriteHCID 516892Sodium BicarbonateHCID 578762518-Methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

生成物 1

HCID 497793773-(8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)propanenitrile収率 61.43%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

8-Methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 8.19 mmol) was taken into water (3 mL) along with acrylonitrile (0.065 mL, 0.982 mmol) and stirred for 10 min. Ceric ammonium nitrite (133 mg, 0.245 mmol) was added to it at once and the reaction mixture was stirred for 2 h. Product was detected by LCMS and TLC. The reaction mixture was basified with sat. NaHCO3 solution and extracted into EtOAc. The organic layer was dried over anhydrous sodium sulfate, concentrated and the crude product purified by column chromatography (Silica gel, 2-4% MeOH in DCM) to get product 180 mg (61.43%). This was converted into the oxalate salt (143 mg). 1HNMR (CD3OD, Oxalate salt) d (ppm): 7.88 (s, 1H), 7.68-7.64 (d, 1H), 7.38-7.34 (d, 1H), 7.22 (s, 1H), 7.18-7.15 (d, 1H), 7.02-6.97 (d, 1H), 4.42 (s, 2H), 4.40-4.36 (t, 2H), 3.58-3.38 (m, 4H), 3.19-3.08 (m, 4H), 2.88-2.80 (t, 2H), 2.53 (s, 3H), 2.40 (s, 3H).

後処理

  1. stirringwas stirred for 2 h
  2. extractionextracted into EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customthe crude product purified by column chromatography (Silica gel, 2-4% MeOH in DCM)

出典と根拠

ORDレコード
ord-19ba9c3e6c304442a231ef40359038f4
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09255094B2

反応ノート

読み込み中…

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