Methyl iodide → 2-(4-bromo-1H-indol-3-yl)propanenitrile

HRID 12618ノート

反応式

HRID 12618 の反応式
O1CCC[CH2:2]1.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH2:23][C:24]#[N:25])=[CH:10][N:11]2C(OC(C)(C)C)=O.C([N-]C(C)C)(C)C.[Li+].CI>O.CO>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:23]([CH3:2])[C:24]#[N:25])=[CH:10][NH:11]2

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 68692455dimethylethyl 4-bromo-3-(cyanomethyl)-1H-indole-1-carboxylate

生成物 1

HCID 686961552-(4-bromo-1H-indol-3-yl)propanenitrile

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a tetrahydrofuran solution (10 mL) of 1, -dimethylethyl 4-bromo-3-(cyanomethyl)-1H-indole-1-carboxylate [CAS registration number 151726-05-5, Organic Letters 2003, 5(19), 3519-3522] (1.0 g), lithium diisopropylamide (2M tetrahydrofuran solution; 3.4 mL) was added dropwise at −78° C. and the mixture was stirred at the same temperature for one hour. To the mixture, methyl iodide (0.5 mL) was added, followed by stirring for one hour. The mixture was gradually heated to room temperature and methanol (2 mL) was added. The mixture was stirred overnight at room temperature and water was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=80:20 y 70:30) to obtain the titled compound having the following physical properties (0.35 g).

後処理

  1. stirringby stirring for one hour
  2. stirringThe mixture was stirred overnight at room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed in turn with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=80:20 y 70:30)

出典と根拠

ORDレコード
ord-0c8396c2e311451a90052e3059475ff1
出典データセット
uspto-grants-2010_06
特許番号
US07728023B2

反応ノート

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