Potassium Phosphate, Tribasic → HCID 67517351, compound
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]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
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
- customTo a 500 ml round bottom flask equipped with a magnetic stir bar
- filtrationUpon completion, the reaction mixture was filtered through celite
- washwashed with water (3×100 ml)
- dry with materialThe organic phase was then dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customto give a crude product
- custompurified
Sources & evidence
- ORD record
- ord-eb5295a164dc4fc6b4c31a88df7ca640
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999966B2
Reaction notes
Loading…