Methyl iodide → (6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

HRID 627309ノート

反応式

HRID 627309 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59227449(6-Bromo-2-nitro-pyridin-3-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 46855854(6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester収率 88.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of (6-bromo-2-nitro-pyridin-3-yl)-carbamic acid tert-butyl ester (6) (290 mg, 0.91 mmol) in DMF (10 mL), NaH (57 mg, 1.36 mmol, 57% dispersion in oil) was added at 0° C. After stirring for 15 minutes, methyl iodide (79 μL, 1.27 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated ammonium chloride solution (15 mL) and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography using 20% ethyl acetate in hexane to give compound (7) (268 mg) as a pale yellow solid.

後処理

  1. stirringthe reaction mixture was stirred for 1 hour
  2. customThe reaction mixture was then quenched with saturated ammonium chloride solution (15 mL)
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-60e3453f36924b73a8596ffa2801bfda
出典データセット
uspto-grants-2016_04
特許番号
US09309267B2

反応ノート

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