Ammonium Chloride → N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

HRID 271889

반응식

HRID 271889 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C(C1C=CC(S([N:36]=[N+:37]=[N-:38])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:36]([C:4]1[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[N+:37]=[N-:38]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 109151434-Dodecylbenzenesulfonyl azideHCID 22293237N-(5-Fluoropyridin-2-yl)pivalamide

생성물 1

HCID 22293288N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a −78° C. solution of N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide (1.34 g, 6.83 mmol) in tetrahydrofuran (25 mL) was added tert-butyl]ithium (1.31 mL of a 1.7 M solution, 20.5 mmol) drop wise. After 3 h at −78° C., 4-dodecylbenzenesulfonyl azide (3.60 g, 10.2 mmol) was added at the reaction was allowed to warm to room temperature. After 1 h, saturated aqueous NH4Cl was added, and the tetrahydrofuran was removed via rotary evaporator. Dichloromethane was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes, then 5%→42% EtOAc/hexanes) to give the title compound (0.275 g). MS 234.0 (M+1).

후처리

  1. waitAfter 1 h
  2. customthe tetrahydrofuran was removed via rotary evaporator
  3. additionDichloromethane was added
  4. customthe layers separated
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-6b88e919b8e04bb2b80c0a83cb4de6a4
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452903B2

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