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

HRID 626302ノート

反応式

HRID 626302 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2aa93a0f16f94c78ba446063a4f7bc73
出典データセット
uspto-grants-2016_04
特許番号
US09309216B2

反応ノート

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