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

HRID 627309노트

반응식

HRID 627309 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60e3453f36924b73a8596ffa2801bfda
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309267B2

반응 노트

불러오는 중…