1-Azido-4-fluorobenzene → HCID 23571068, compound

HRID 1823997Notes

Reaction equation

HRID 1823997 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:13][C@H:12]3[C@:14]4([CH2:18][N:17]([CH2:19][C:20]([F:23])([F:22])[F:21])[S:16](=[O:25])(=[O:24])[NH:15]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8][C:7]=2[CH:26]=1)#[CH:2].[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[N+:35]=[N-:36])=[CH:30][CH:29]=1>CC1C=CC(C)=CC=1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:2]=[C:1]([C:3]3[CH:4]=[CH:5][C:6]4[CH2:13][C@H:12]5[C@:14]6([CH2:18][N:17]([CH2:19][C:20]([F:21])([F:22])[F:23])[S:16](=[O:25])(=[O:24])[NH:15]6)[C@H:9]([CH2:10][CH2:11]5)[CH2:8][C:7]=4[CH:26]=3)[N:36]=[N:35]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 108879741-Azido-4-fluorobenzeneHCID 23571114HCID 23571114, compound

Product 1

HCID 23571068HCID 23571068, compound

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of the alkyne from Step 2 (0.075 g, 0.195 mmol) and 4-fluorophenylazide (0.035 g, 0.25 mmol) in p-xylene (5 mL) was refluxed under nitrogen for 21 hr. The solution was evaporated to dryness. Preparative HPLC on a normal phase column, eluting with an ethyl acetate-isohexane gradient gave the major cycloadduct (0.022 g). Further purification by reverse phase HPLC, eluting with an acetonitrile-pH3 buffer gradient, gave the triazole as yellow solid, which was rinsed with diethyl ether and dried to give a pale yellow powder (0.010 g, 10%).

Workup

  1. customThe solution was evaporated to dryness
  2. washPreparative HPLC on a normal phase column, eluting with an ethyl acetate-isohexane gradient
  3. customgave the major cycloadduct (0.022 g)
  4. customFurther purification by reverse phase HPLC
  5. washeluting with an acetonitrile-pH3 buffer gradient

Sources & evidence

ORD record
ord-4d65f663084e4a818427cbdbf7b18c9e
Source dataset
uspto-grants-2006_05
Patent number
US07041689B2

Reaction notes

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