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

HRID 243579노트

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HRID 243579 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a97e9c2ef1cc45d788c854168af193d7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653274B2

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