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Potassium Phosphate, Tribasic → HCID 67517351, compound

HRID 1465691
Notes
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Reaction equation

HRID 1465691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[C:5]2I.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:22]1[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 53439660tert-Butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate

Product 1

HCID 67517351HCID 67517351, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 500 ml round bottom flask equipped with a magnetic stir bar was added tert-butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate (6.00 g, 14.2 mmol), followed by the additions of 4-pyridineboronic acid (1.92 g, 15.6 mmol), PdCl2(dppf) (1.16 g, 1.4 mmol) and K3PO4 (9.03 g, 42.5 mmol). The mixture was dissolved in a mixture of 160 ml of dioxane and 40 ml of H2O and stirred overnight at 80° C. Upon completion, the reaction mixture was filtered through celite and washed with water (3×100 ml). The organic phase was then dried over anhydrous MgSO4, filtered and concentrated to dryness to give a crude product. The crude product was column purified to give 5-bromo-3-(pyridin-4-yl)-1H-indazole (2.74 g) as a de-BOc product.

Workup

  1. customTo a 500 ml round bottom flask equipped with a magnetic stir bar
  2. filtrationUpon completion, the reaction mixture was filtered through celite
  3. washwashed with water (3×100 ml)
  4. dry with materialThe organic phase was then dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customto give a crude product
  8. custompurified

Sources & evidence

ORD record
ord-eb5295a164dc4fc6b4c31a88df7ca640
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999966B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes