Iodoethane → 1-ethyl-6-methoxy-1H-indole-3-carbonitrile

HRID 505987ノート

反応式

HRID 505987 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:16](I)[CH3:17]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[CH:8][N:9]2[CH2:16][CH3:17])=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 534011976-Methoxy-1H-indole-3-carbonitrile

生成物 1

HCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 6-methoxyindole (10.0 g, 68.0 mmol) in DMF (120 mL) is cooled to 0° C. and treated with chlorosulfonyl isocyanate (7.72 mL, 88.4 mmol). After the addition, the reaction mixture is stirred at this temperature for 1 h. The dark solution is poured into ice water (600 mL) and the light brown solid is collected by filtration, washed with additional H2O and dried to afford 9.9 g (85%) of 6-methoxy-1H-indole-3-carbonitrile as a light brown solid. Step B: To a solution of 6-methoxy-1H-indole-3-carbonitrile (9.9 g, 57.6 mmol) in DMF (150 mL) is added NaH (60% dispersion in mineral oil, 3.45 g, 86.3 mmol). The reaction mixture is stirred for 15 min and then ethyl iodide (5.53 mL, 69.1 mmol) is added and the mixture is stirred at room temperature overnight. The reaction mixture is then diluted with H2O and extracted with EtOAc (2×). The organic phases are washed with H2O (3×) and saturated NaCl and then dried and concentrated to a semi-solid. The crude product is purified via column chromatography on silica gel (200 g) using CH2Cl2/hexanes (50-100%) as eluent to yield 6-methoxy-1-ethyl-1H-indole-3-carbonitrile as a tan solid.

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionextracted with EtOAc (2×)
  3. washThe organic phases are washed with H2O (3×) and saturated NaCl
  4. customdried
  5. concentrationconcentrated to a semi-solid
  6. customThe crude product is purified via column chromatography on silica gel (200 g)

出典と根拠

ORDレコード
ord-f5464dd6616f49d499b0022af73d62e7
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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