Methyl iodide → (5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

HRID 243579ノート

反応式

HRID 243579 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I.[NH4+].[Cl-]>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 56924569(5-Bromo-6-nitro-pyridin-2-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 46183971(5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester収率 94.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of (5-bromo-6-nitro-pyridin-2-yl)-carbamic acid tert-butyl ester (11) (800 mg, 2.52 mmol) in dry DMF (15 mL), NaH (60% dispersion in mineral oil, 191 mg, 4.53 mmol) was added at 0° C. The resulting mixture was stirred for 30 minutes at 0° C. and methyl iodide (0.23 mL, 3.68 mmol) was then added. After stirring the reaction mixture for 30 minutes at 10° C., saturated aqueous NH4Cl (15 mL) was added. The reaction mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water, brine, dried over MgSO4 (anhydrous) and concentrated under reduced pressure. The crude product was purified by Biotage using 10% ethyl acetate in hexane to afford (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester 12 (789 mg).

後処理

  1. stirringAfter stirring the reaction mixture for 30 minutes at 10° C.
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×30 mL)
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over MgSO4 (anhydrous)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by Biotage

出典と根拠

ORDレコード
ord-a97e9c2ef1cc45d788c854168af193d7
出典データセット
uspto-grants-2014_02
特許番号
US08653274B2

反応ノート

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