Sodium hydride → 7-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-2,3,5,6,7,11c-hexahydro-1H-pyrido[3',2':4,5]pyrrolo[2,3-g]indolizine

HRID 535877ノート

反応式

HRID 535877 の反応式
[CH2:1]1[CH:16]2[N:4]([CH2:5][CH2:6][C:7]3[NH:8][C:9]4[N:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15]=32)[CH2:3][CH2:2]1.[H-].[Na+].[O:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>CN(C=O)C>[N:25]1[CH:26]=[CH:27][C:22]([CH:20]([OH:19])[CH2:21][N:8]2[C:7]3[CH2:6][CH2:5][N:4]4[CH:16]([C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=3)[CH2:1][CH2:2][CH2:3]4)=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 109534834-(Oxiran-2-yl)pyridineHCID 670366062,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene

生成物 1

HCID 584598877-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-2,3,5,6,7,11c-hexahydro-1H-pyrido[3',2':4,5]pyrrolo[2,3-g]indolizine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 2,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene (1 g, 4.6 mmol) in DMF (20 mL) were portion wise added NaH (60%, 0.552 g, 13.8 mmol) and 4-(oxiran-2-yl)pyridine (0.709 g, 5.6 mmol). The reaction mass was stirred at RT overnight. The progress of reaction was monitored by LCMS. The reaction mixture was quenched with ice cold water (300 mL) and extracted with EtOAc (3×100 mL). The combined organic layer was washed with water (10×100 mL), followed by brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography followed by reverse phase HPLC to yield the title compound;

後処理

  1. customThe progress of reaction
  2. customThe reaction mixture was quenched with ice cold water (300 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with water (10×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-094cb822ea954d7ea7facd48ec01ca05
出典データセット
uspto-grants-2014_10
特許番号
US08859561B2

反応ノート

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