Sodium Azide → (R)-2-(1-azidoethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

HRID 626302노트

반응식

HRID 626302 반응식
[NH2:1][C@@H:2]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:21])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[C:10]([F:22])[CH:9]=[CH:8][CH:7]=2)[CH3:3].CS(O[C@@H](C1OC2C(C(=O)C=1C1C=CC=C(F)C=1)=C(F)C=CC=2)C)(=O)=O.[N-:49]=[N+:50]=[N-].[Na+]>CN(C=O)C>[N:1]([C@@H:2]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:21])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[C:10]([F:22])[CH:9]=[CH:8][CH:7]=2)[CH3:3])=[N+:49]=[N-:50]

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 117970485(R)-2-(1-aminoethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-oneHCID 131735211(R)-1-(5-fluoro-3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl)ethyl methane sulfonate

생성물 1

HCID 131735212(R)-2-(1-azidoethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of (S)/(R)-1-(5-fluoro-3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl)ethyl methane sulfonate (0.900 g, 2.36 mmol) in DMF (18 ml), sodium azide (0.306 g, 4.72 mmol) is added and heated to 60° C. After 2 h, the reaction mass is quenched with water, extracted with dichloromethane, dried over sodium sulphate and concentrated. The crude product is column chromatographed with ethyl acetate:petroleum ether to afford the title compound as a brown liquid which is used as such in next step.

후처리

  1. customthe reaction mass is quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customchromatographed with ethyl acetate

출처 및 근거

ORD 기록
ord-2aa93a0f16f94c78ba446063a4f7bc73
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309216B2

반응 노트

불러오는 중…