Potassium Phosphate, Tribasic → 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole

HRID 1465683Notes

Reaction equation

HRID 1465683 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=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.[N:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=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]>[N+:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[N:3]=[C:2]2[C:36]1[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=1)([O-:13])=[O:12]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 589464433-bromo-5-nitro-1-trityl-1H-indazole

Product 1

HCID 601460255-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazoleYield 81.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 500 ml round bottom flask equipped with a magnetic stir bar was added 3-bromo-5-nitro-1-trityl-1H-indazole (13.13 g, 27.1 mmol), followed by the additions of 4-pyridine boronic acid (5.00 g, 40.7 mmol), PdCl2(dppf) (2.21 g, 2.7 mmol) and K3PO4 (14.39 g, 67.8 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 a pad of celite and washed with water (3×100 ml). The organic phase was then dried over anhydrous MgSO4, filtered and concentrated to give a crude product. The crude product was column purified (30% EtAOc/Hexane) to give 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole (10.7 g) as a yellow solid.

Workup

  1. customTo a 500 ml round bottom flask equipped with a magnetic stir bar
  2. filtrationUpon completion, the reaction mixture was filtered through a pad of celite
  3. washwashed with water (3×100 ml)
  4. dry with materialThe organic phase was then dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product
  8. custompurified (30% EtAOc/Hexane)

Sources & evidence

ORD record
ord-95b4d317195f410aa51761173747afc1
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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