Potassium Hydroxide → HCID 89526503, compound

HRID 571371Notes

Reaction equation

HRID 571371 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9](C(O)=O)=[CH:10][C:5]=2[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.C1(P([N:47]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[OH-].[K+]>O1CCOCC1>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:47])=[CH:10][C:5]=2[N:4]([C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 895259173-Bromo-1-(triphenylmethyl)-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid

Product 1

HCID 89526503HCID 89526503, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid (1.95 g, 4.03 mmol) in 1,4-dioxane (19.50 mL) and diphenylphosphoryl azide (DPPA) (1.047 mL, 4.83 mmol), TEA (0.842 mL, 6.04 mmol) in 10 mL of 1,4-dioxane was added dropwise over 5 min. The clear solution was heated to 80° C. for 2 h and a yellow clear solution was obtained. A solution of 1N KOH (20.13 mL, 20.13 mmol) was added at the same temperature. The reaction mixture was heated to 80° C. overnight. After cooling down to room temperature, the reaction mixture was extracted with EtOAc. The combined organic layer was washed with brine and then dried (Na2SO4). After filtration and removal of solvent, the residue was purified by column chromatography on silica gel 50 g, eluting with 50% EtOAc in hexane to give the product 9a as an off white solid (0.61 g, 1.34 mmol, 33%). MS ESI calc'd. for C25H20BrN4 [M+H]+455, found 455.

Workup

  1. additionwas added dropwise over 5 min
  2. customa yellow clear solution was obtained
  3. temperatureThe reaction mixture was heated to 80° C. overnight
  4. temperatureAfter cooling down to room temperature
  5. extractionthe reaction mixture was extracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationAfter filtration and removal of solvent
  9. customthe residue was purified by column chromatography on silica gel 50 g
  10. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-017672fe84ed442ebc8cdaaaf808f583
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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