Pyrazolo[1,5-a]pyridine, 3-bromo-6-chloro-2-(4-fluorophenyl)- → HCID 9909053, compound

HRID 2300199Notes

Reaction equation

HRID 2300199 reaction equation
Br[C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:5]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=12.C([Sn](CCCC)(CCCC)[C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)CCC>O1CCOCC1.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C(C)C(P(C2C=CC=CC=2)C2C=CC=CC=2)C)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([N:4]=[C:3]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:2]=2[C:24]2[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:10]=1

Participants

7

Reactant 2

HCID 18376027Pyrazolo[1,5-a]pyridine, 3-bromo-6-chloro-2-(4-fluorophenyl)-HCID 18768487HCID 18768487, compound

Product 1

HCID 9909053HCID 9909053, compoundYield 34%

Reagents, catalysts & solvents 4

HCID 92152Silver(II) oxideCatalystHCID 131723721HCID 131723721, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-6-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine (397 mg, 1.22 mmol), 4-(tri-n-butylstannyl)phenylsulfonamide (1.09 g), bis(diphenylphosphino)butane palladium(II) dichloride (100 mg) and silver oxide (283 mg) were stirred in anhydrous dioxan (15 ml) at reflux for 24 h. After cooling, the concentrated reaction mixture was taken up in DCM and concentrated onto silica gel which was loaded onto an SPE column and eluted with cyclohexane:ethyl acetate (8:1). This gave a white solid which was triturated with cyclohexane and filtered to give the title compound as a white solid (165 mg, 34%). MH+ 400 1H NMR (DMSO) δ 7.27 (2H, t, J 8 Hz); 7.4 (3H, m); 7.52 (4H, m); 7.7 (1H, d, J 9 Hz); 7.87 (2H, d, J 8 Hz); 9.18 (1H, s); Tlc SiO2 cyclohexane:ethyl acetate (3:1) Rf 0.12 detection uv254.

Workup

  1. temperatureat reflux for 24 h
  2. temperatureAfter cooling
  3. customthe concentrated reaction mixture
  4. concentrationconcentrated onto silica gel which
  5. washeluted with cyclohexane:ethyl acetate (8:1)
  6. customThis gave a white solid which
  7. customwas triturated with cyclohexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c957ef8723ae466a9fc50d2d3c40ccfc
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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