(Diethylamino)sulfur trifluoride → HCID 178505389, compound

HRID 2243308Notes

Reaction equation

HRID 2243308 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15](O)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C(N(S(F)(F)[F:30])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[F:30][CH:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:2]3[NH:1][C:9]4[CH:8]=[CH:7][N:6]=[CH:5][C:4]=4[N:3]=3)[C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59208216HCID 59208216, compound

Product 1

HCID 178505389HCID 178505389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10-ml round-bottomed flask under an argon atmosphere, dissolve 85 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-ol, obtained in Example 3, in 3 ml of dichloromethane. Cool the solution obtained to −60° C. then add, dropwise using a syringe, 41 μL of diethylamino sulphur trifluoride (DAST). Leave to return to room temperature and stir for 45 minutes, then pour the reaction mixture into an aqueous solution with 10% of sodium hydrogen carbonate and extract twice with dichloromethane. Combine the organic phases, dry over sodium sulphate and concentrate under reduced pressure. After purification by chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (95-5 by volume), we obtain 44 mg of 2-[9(R,S)-fluoro-9H-fluoren-4-yl]-1H-imidazo[4,5-c]pyridine, in the form of a white powder with the following characteristics:

Workup

  1. temperatureCool the solution
  2. customobtained to −60° C.
  3. additionthen add
  4. customLeave
  5. customto return to room temperature
  6. extractionextract twice with dichloromethane
  7. dry with materialdry over sodium sulphate
  8. concentrationconcentrate under reduced pressure
  9. customAfter purification by chromatography on silica gel (40-63 μm)
  10. washeluting with a mixture of dichloromethane and methanol (95-5 by volume), we

Sources & evidence

ORD record
ord-7ee3ed8d629240a6b1c92821cd007647
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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