Ethyl Acetate → 1,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamate

HRID 1984705

반응식

HRID 1984705 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37](CO)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(OCC)(=O)C>C(Cl)Cl>[Br:24][CH2:20][C:37]1[CH:36]=[CH:35][N:34]=[C:33]([NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH:38]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridine

생성물 1

HCID 220977361,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamate수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triphenylphosphine (970 mg, 3.7 mmol) and carbon tetrabromide (1.5 g, 4.6 mmol) were added to a solution of (2-tert-butoxycarbonylaminopyridin-4-yl)methanol (Reference compound No. 4-1, 690 mg, 3.1 mmol) in methylene chloride (20 mL) under ice-cooling, and the mixture was stirred for 2 hours at room temperature. Ethyl acetate (30 mL) was added to the reaction mixture, the whole was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL), and then dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting solid was filtered off with ethyl acetate to give 550 mg of the title reference compound as a colorless solid. (Yield 62%)

후처리

  1. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. filtrationthe resulting solid was filtered off with ethyl acetate
  5. customto give 550 mg of the title reference compound as a colorless solid

출처 및 근거

ORD 기록
ord-0f5a3073906945fdb8b62484d3049fa9
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544703B2

연결된 노트

불러오는 중…