Ammonium Chloride → 1-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

HRID 538342노트

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HRID 538342 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:16])([CH3:15])[CH2:9]OS(C)(=O)=O)[C:5]([F:17])=[CH:4][N:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[NH4+].[Cl-]>C(O)C.O.CC(OC)(C)C>[N:18]([CH2:9][C:8]([C:6]1[C:5]([F:17])=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)([OH:16])[CH3:15])=[N+:19]=[N-:20]

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86668051Methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester

생성물 1

HCID 866680521-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 15413tert-Butyl methyl ether용매

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온도
80 °C

실험 절차

To a solution of methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester (10.36 g, 31.6 mmol) in ethanol (160 ml) was added NaN3 (5.13 g, 79.0 mmol) and NH4Cl (8.44 g, 158.0 mmol). The reaction mixture was stirred at 80° C. for 20 h. The reaction mixture was diluted with H2O and TBME and the phases were separated. The aq. phase was twice reextracted with TBME, the combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated. HPLC RtH4=0.89 min; ESIMS: 275, 277 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.20 (d, 1H), 7.80 (d, 1H), 3.81 (d, 1H), 3.65 (d, 1H), 1.61 (s, 3H).

후처리

  1. customthe phases were separated
  2. washphases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC RtH4=0.89 min

출처 및 근거

ORD 기록
ord-cc08395313244554829551367d9f3f40
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865712B2

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