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

HRID 626302Notes

Reaction equation

HRID 626302 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2aa93a0f16f94c78ba446063a4f7bc73
Source dataset
uspto-grants-2016_04
Patent number
US09309216B2

Reaction notes

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