Sodium Iodide → 5-Bromo-1-(3-(tert-butyldimethylsilyloxy)-1-phenylpropyl)-3-nitro-1H-1,2,4-triazole

HRID 451491ノート

反応式

HRID 451491 の反応式
Br[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Br:27][C:28]1[NH:32][N:31]=[C:30]([N+:33]([O-:35])=[O:34])[N:29]=1>C(#N)C.O>[Br:27][C:28]1[N:32]([CH:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[N:31]=[C:30]([N+:33]([O-:35])=[O:34])[N:29]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 67335370(3-Bromo-3-phenylpropoxy)(tert-butyl)dimethylsilaneHCID 178526904HCID 178526904、化合物

生成物 1

HCID 673344335-Bromo-1-(3-(tert-butyldimethylsilyloxy)-1-phenylpropyl)-3-nitro-1H-1,2,4-triazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of (3-bromo-3-phenylpropoxy)(tert-butyl)dimethylsilane (934 mg, 2.84 mmol) in acetonitrile (27 mL) was stirred at room temperature under an atmosphere of nitrogen with sodium iodide (425 mg, 2.84 mmol) for 15 minutes. Potassium carbonate (560 mg, 4.05 mmol) was added and the reaction was heated 60° C. At this temperature 5-bromo-3-nitro-1H-1,2,4-triazole (532 mg, 2.7 mmol) dissolved in acetonitrile (5.3 mL) was added within 30 minutes. The reaction was stirred for 2 hours at 85° C. Water was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a colorless viscous oil (510 mg, 42%) after column chromatography on silica gel using a gradient from heptane to heptane/ethyl acetate 4:1 (v/v) as eluent. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.42-7.36 (m, 5H), 5.91 (dd, 1H), 3.58 (m, 1H), 3.48 (m, 1H), 2.72 (m, 1H), 2.39 (m, 1H), 0.91 (s, 9H), 0.00 (s, 6H).

後処理

  1. additionwas added within 30 minutes
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-afdf04c3923c4c4ebe070c1f59474289
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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