Ethyl Acetate → HCID 59425449、化合物

HRID 506098ノート

反応式

HRID 506098 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.[P:24](Cl)([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>O1CCOCC1>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH3:21])=[CH:13][CH:14]=2)[N:9]([CH2:22][CH3:23])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][P:24](=[O:25])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:7][CH:6]=1)#[N:18]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 13139Diethyl chlorophosphateHCID 81531DiisopropylethylamineHCID 594252742-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

生成物 1

HCID 59425449HCID 59425449、化合物収率 51%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (148 mg, 0.484 mmol), diethyl chlorophosphate (0.086 mL, 0.58 mmol) and diisopropylethylamine (0.10 mL, 0.57 mmol) in 1,4-dioxane (5 mL) is stirred at ambient temperature for 12 hours, then heated to 80° C. for an additional 24 hours. The solution is cooled and poured into 50 mL of ethyl acetate. This is washed with water and saturated brine (50 mL each), then dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material is separated by flash chromatography (eluting 2/1 ethyl acetate/hexane on silica gel 60) to afford diethyl [4-(3-cyano-6-ethoxy-1-ethyl-1H-indol-2-yl)-phenyl]-phosphoramidate (108 mg, 0.245 mmol, 51%) as a white powder after evaporation.

後処理

  1. temperatureThe solution is cooled
  2. washThis is washed with water and saturated brine (50 mL each)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual material is separated by flash chromatography (eluting 2/1 ethyl acetate/hexane on silica gel 60)

出典と根拠

ORDレコード
ord-8f7a1599d2ff43f78494414714bc9251
出典データセット
uspto-grants-2010_08
特許番号
US07781478B2

反応ノート

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